DD283807A5 - Verfahren zur herstellung von cycloalkyl-substituierten glutaramid-derivaten - Google Patents

Verfahren zur herstellung von cycloalkyl-substituierten glutaramid-derivaten Download PDF

Info

Publication number: DD283807A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; group; formula; cis; lysyl
Prior art date: 1988-05-27

Application number

DD89328909A

Other languages

German (de)

English (en)

Inventor

James Keith

John Ch Danilewicz

Original Assignee

��@��Kk��

Priority date (The priority date 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 date listed.)

1988-05-27

Filing date

1989-05-25

Publication date

1990-10-24

1989-05-25 Application filed by ��@��Kk�� filed Critical ��@��Kk��

1990-10-24 Publication of DD283807A5 publication Critical patent/DD283807A5/de

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RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical class NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 title claims abstract description 9
238000004519 manufacturing process Methods 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 78
238000000034 method Methods 0.000 claims abstract description 51
238000002360 preparation method Methods 0.000 claims abstract description 11
-1 piperidino, morpholino, piperazinyl Chemical group 0.000 claims description 59
229910052799 carbon Inorganic materials 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 27
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
125000000623 heterocyclic group Chemical group 0.000 claims description 14
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
229920006395 saturated elastomer Polymers 0.000 claims description 12
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 9
101150065749 Churc1 gene Proteins 0.000 claims description 9
102100038239 Protein Churchill Human genes 0.000 claims description 9
230000007062 hydrolysis Effects 0.000 claims description 9
238000006460 hydrolysis reaction Methods 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 6
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
125000002837 carbocyclic group Chemical group 0.000 claims description 3
125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
125000001425 triazolyl group Chemical group 0.000 claims description 3
125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
238000010511 deprotection reaction Methods 0.000 claims description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 2
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 2
239000001294 propane Substances 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 claims 3
239000003513 alkali Substances 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
239000002934 diuretic Substances 0.000 abstract description 9
229940030606 diuretics Drugs 0.000 abstract description 5
239000003814 drug Substances 0.000 abstract description 4
229910052727 yttrium Inorganic materials 0.000 abstract description 4
239000000137 peptide hydrolase inhibitor Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
238000004458 analytical method Methods 0.000 description 29
239000000047 product Substances 0.000 description 27
239000000243 solution Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
150000002148 esters Chemical class 0.000 description 12
239000000203 mixture Substances 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
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102400001282 Atrial natriuretic peptide Human genes 0.000 description 8
101800001890 Atrial natriuretic peptide Proteins 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
206010019280 Heart failures Diseases 0.000 description 7
NSQLIUXCMFBZME-MPVJKSABSA-N carperitide Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(O)=O)=O)[C@@H](C)CC)C1=CC=CC=C1 NSQLIUXCMFBZME-MPVJKSABSA-N 0.000 description 7
239000007858 starting material Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
206010020772 Hypertension Diseases 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
208000001647 Renal Insufficiency Diseases 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
201000006370 kidney failure Diseases 0.000 description 6
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238000003756 stirring Methods 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
102000003729 Neprilysin Human genes 0.000 description 5
108090000028 Neprilysin Proteins 0.000 description 5
239000012043 crude product Substances 0.000 description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
230000015556 catabolic process Effects 0.000 description 4
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229920001971 elastomer Polymers 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
239000005541 ACE inhibitor Substances 0.000 description 3
241000282412 Homo Species 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 3
239000012267 brine Substances 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
238000006731 degradation reaction Methods 0.000 description 3
150000005690 diesters Chemical class 0.000 description 3
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229910052763 palladium Inorganic materials 0.000 description 3
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
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125000001424 substituent group Chemical group 0.000 description 3
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QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
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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 description 2
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239000012359 Methanesulfonyl chloride Substances 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
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FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
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JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
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125000005843 halogen group Chemical group 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000005556 hormone Substances 0.000 description 2
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QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
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125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 description 1
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WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/06—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0207—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)4-C(=0), e.g. 'isosters', replacing two amino acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Biochemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Crystallography & Structural Chemistry (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hematology (AREA)
Reproductive Health (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Immunology (AREA)
Epidemiology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (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)
Pyridine Compounds (AREA)
Pyrrole Compounds (AREA)

DD89328909A 1988-05-27 1989-05-25 Verfahren zur herstellung von cycloalkyl-substituierten glutaramid-derivaten DD283807A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888812597A GB8812597D0 (en)	1988-05-27	1988-05-27	Therapeutic agents

Publications (1)

Publication Number	Publication Date
DD283807A5 true DD283807A5 (de)	1990-10-24

Family

ID=10637649

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89328909A DD283807A5 (de)	1988-05-27	1989-05-25	Verfahren zur herstellung von cycloalkyl-substituierten glutaramid-derivaten

Country Status (15)

Country	Link
US (2)	US4960792A (fr)
EP (1)	EP0343911A3 (fr)
JP (1)	JPH0242047A (fr)
KR (1)	KR900017994A (fr)
CN (1)	CN1038103A (fr)
AU (1)	AU601332B2 (fr)
DD (1)	DD283807A5 (fr)
DK (1)	DK257089A (fr)
FI (1)	FI892579A7 (fr)
GB (1)	GB8812597D0 (fr)
HU (1)	HU202194B (fr)
IL (1)	IL90344A0 (fr)
NO (1)	NO892140L (fr)
PL (1)	PL279614A1 (fr)
PT (1)	PT90645A (fr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8820844D0 (en) *	1988-09-05	1988-10-05	Pfizer Ltd	Therapeutic agents
GB8926512D0 (en) *	1989-11-23	1990-01-10	Pfizer Ltd	Therapeutic agents
GB9000725D0 (en) *	1990-01-12	1990-03-14	Pfizer Ltd	Therapeutic agents
GB9004260D0 (en) *	1990-02-26	1990-04-18	Pfizer Ltd	Therapeutic agents
AU1870292A (en) *	1991-04-16	1992-11-17	Schering Corporation	Use of neutral endopeptidase inhibitors in the treatment of nephrotoxicity
US5298492A (en) *	1992-08-04	1994-03-29	Schering Corporation	Diamino acid derivatives as antihypertensives
US5208236A (en) *	1992-09-23	1993-05-04	Schering Corporation	N-(acylaminomethyl)glutaryl amino acids and use
AU751950B2 (en) *	1997-11-24	2002-09-05	Merck & Co., Inc.	Substituted beta-alanine derivatives as cell adhesion inhibitors
US6645939B1 (en)	1997-11-24	2003-11-11	Merck & Co., Inc.	Substituted β-alanine derivatives as cell adhesion inhibitors
JP2005022976A (ja) *	2001-07-18	2005-01-27	Ajinomoto Co Inc	カルボン酸誘導体
US7468390B2 (en)	2002-01-17	2008-12-23	Novartis Ag	Methods of treatment and pharmaceutical composition
US7899527B2 (en) *	2004-05-13	2011-03-01	Palo Alto Investors	Treatment of conditions through modulation of the autonomic nervous system during at least one predetermined menstrual cycle phase
US20100260669A1 (en) *	2004-05-13	2010-10-14	Anthony Joonkyoo Yun	Treatment of Seasonal Conditions Through Modulation of the Autonomic Nervous System
AR057882A1 (es)	2005-11-09	2007-12-26	Novartis Ag	Compuestos de accion doble de bloqueadores del receptor de angiotensina e inhibidores de endopeptidasa neutra
AU2013304949C1 (en)	2012-08-24	2020-12-24	Novartis Ag	NEP inhibitors for treating diseases characterized by atrial enlargement or remodeling
WO2017033128A1 (fr)	2015-08-25	2017-03-02	Novartis Ag	Dérivés d'acide 4-aminé-butyrique substitués par le biphényle, et leur utilisation dans la synthèse d'inhibiteurs de nep
US20180311241A1 (en)	2015-10-29	2018-11-01	Cadila Healthcare Limited	Pharmaceutical synergistic combination

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3981915A (en) *	1971-12-17	1976-09-21	American Home Products Corporation	Amides of 1-aminocyclopentane carboxylic acid
KR880007441A (ko) *	1986-12-11	1988-08-27	알렌 제이.스피겔	스피로-치환된 글루타르아미드 이뇨제
GB8811873D0 (en) *	1988-05-19	1988-06-22	Pfizer Ltd	Therapeutic agents
GB8820844D0 (en) *	1988-09-05	1988-10-05	Pfizer Ltd	Therapeutic agents

1988
- 1988-05-27 GB GB888812597A patent/GB8812597D0/en active Pending
1989
- 1989-05-08 US US07/349,025 patent/US4960792A/en not_active Expired - Lifetime
- 1989-05-19 IL IL90344A patent/IL90344A0/xx unknown
- 1989-05-23 EP EP19890305180 patent/EP0343911A3/fr not_active Withdrawn
- 1989-05-24 PL PL27961489A patent/PL279614A1/xx unknown
- 1989-05-24 PT PT90645A patent/PT90645A/pt not_active Application Discontinuation
- 1989-05-25 DD DD89328909A patent/DD283807A5/de not_active IP Right Cessation
- 1989-05-25 HU HU892672A patent/HU202194B/hu not_active IP Right Cessation
- 1989-05-26 FI FI892579A patent/FI892579A7/fi not_active Application Discontinuation
- 1989-05-26 DK DK257089A patent/DK257089A/da not_active Application Discontinuation
- 1989-05-26 AU AU35240/89A patent/AU601332B2/en not_active Expired - Fee Related
- 1989-05-26 NO NO89892140A patent/NO892140L/no unknown
- 1989-05-27 CN CN89103709A patent/CN1038103A/zh active Pending
- 1989-05-27 KR KR1019890007117A patent/KR900017994A/ko not_active Ceased
- 1989-05-29 JP JP1135708A patent/JPH0242047A/ja active Pending
1990
- 1990-06-14 US US07/538,357 patent/US5036104A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU601332B2 (en)	1990-09-06
FI892579A0 (fi)	1989-05-26
PT90645A (pt)	1989-11-30
DK257089A (da)	1990-01-25
EP0343911A2 (fr)	1989-11-29
PL279614A1 (en)	1989-12-11
FI892579A7 (fi)	1989-11-28
JPH0242047A (ja)	1990-02-13
DK257089D0 (da)	1989-05-26
US4960792A (en)	1990-10-02
NO892140D0 (no)	1989-05-26
HUT50106A (en)	1989-12-28
NO892140L (no)	1989-11-28
KR900017994A (ko)	1990-12-20
IL90344A0 (en)	1989-12-15
US5036104A (en)	1991-07-30
HU202194B (en)	1991-02-28
EP0343911A3 (fr)	1991-01-16
CN1038103A (zh)	1989-12-20
AU3524089A (en)	1989-11-30
GB8812597D0 (en)	1988-06-29

Legal Events

Date	Code	Title	Description
1994-11-10	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69417049T2 (de)	1999-09-16	Hydroxamsäurederivate als inhibitoren von cylokine produktion
DD283807A5 (de)	1990-10-24	Verfahren zur herstellung von cycloalkyl-substituierten glutaramid-derivaten
US5362902A (en)	1994-11-08	N-(1-(2-carboxyethyl35cloalkylcarbonyl)-beta-alanine derivatives for pharmaceutical use
DD284222A5 (de)	1990-11-07	Verfahren zur herstellung von cycloalkylsubstituierten glutaramidderivaten
DE69511240T2 (de)	1999-12-09	Derivate des hydroxamsäure als metalloproteinaseinhibitoren
DE69509254T2 (de)	1999-09-23	Metalloproteinase-inhibitoren
DE3508251A1 (de)	1986-09-11	Dipeptide
DD236522A5 (de)	1986-06-11	Verfahren zur herstellung medizinisch wertvoller verbindungen und zwischenverbindungen
WO1993004035A1 (fr)	1993-03-04	Nouveaux derives 3,5-di-tert.butyl-4-hydroxyphenyles, leur procede de fabrication et medicaments les renfermant
DD216717A5 (de)	1984-12-19	Verfahren zur herstellung von benzazocinon- und benzazoninon-derivaten
DE3783280T2 (de)	1993-05-06	Teilweise retro-invertierte analoge des tuftsin, methode zu ihrer herstellung und pharmazeutische zusammensetzungen, die sie enthalten.
EP0796271B1 (fr)	2000-02-02	p-amidinobenzylamides dipeptidiques a restes n-terminaux sulfonyle ou aminosulfonyle
DE69715886T2 (de)	2003-05-15	Acylaminoalkenylen-amid-derivate als nk1 und nk2 antagonisten
EP0144290A2 (fr)	1985-06-12	Dérivés éthylènediamine substitués
DE2660626C2 (de)	1985-07-11	3-Amino-2-hydroxy-4-phenyl-butansäure-Derivate und Verfahren zu ihrer Herstellung
EP0115472A2 (fr)	1984-08-08	Dérivés de la pyrrolidinone et leur procédé de préparation
DE2515146A1 (de)	1976-10-21	Carbonsaeureamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE69610836T2 (de)	2001-04-19	Matrix-metallprotease inhibitoren
DE2112057A1 (de)	1971-09-23	Neue Penicillinester
DE3737399A1 (de)	1989-05-18	Aminosaeureester, verfahren zu ihrer herstellung und ihre verwendung
EP1483285A1 (fr)	2004-12-08	INHIBITEURS DU FACTEUR DE COAGULATION Xa, LEUR PRODUCTION ET LEUR UTILISATION
WO1991010644A1 (fr)	1991-07-25	Agents diuretiques a base de glutaramide a substitution cycloalkyle
DE69724112T2 (de)	2004-06-03	Peptidverbindungen mit mmp- und tnf-hemmender wirkung
DE69027460T2 (de)	1996-10-10	Peptidderivate und deren pharmazeutische Verwendung
DE69015208T2 (de)	1995-05-04	Glutamin- und asparginsäurederivate mit antigastrinwirkung und verfahren zu deren herstellung.