NL7920076A - Cyclische iminocarbonzuurderivaten. - Google Patents

Cyclische iminocarbonzuurderivaten. Download PDF

Info

Publication number: NL7920076A
Authority: NL; Netherlands
Prior art keywords: acid; formula; chloro; salt; cyclic
Prior art date: 1978-10-05

Application number

NL7920076A

Other languages

English (en)

Dutch (nl)

Original Assignee

Yoshitomi Pharmaceutical

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.)

1978-10-05

Filing date

1979-09-28

Publication date

1980-08-29

1979-09-28 Application filed by Yoshitomi Pharmaceutical filed Critical Yoshitomi Pharmaceutical

1980-08-29 Publication of NL7920076A publication Critical patent/NL7920076A/nl

Links

KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title 1
-1 nitro, amino Chemical group 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 18
229960002429 proline Drugs 0.000 claims description 11
125000004122 cyclic group Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
ULSZVNJBVJWEJE-GSVOUGTGSA-N (2r)-1,3-thiazolidin-3-ium-2-carboxylate Chemical compound [O-]C(=O)[C@@H]1[NH2+]CCS1 ULSZVNJBVJWEJE-GSVOUGTGSA-N 0.000 claims description 3
229930182821 L-proline Natural products 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
150000001875 compounds Chemical class 0.000 description 12
239000000203 mixture Substances 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000000843 powder Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
238000001816 cooling Methods 0.000 description 6
238000000034 method Methods 0.000 description 6
239000000284 extract Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000013078 crystal Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000017550 sodium carbonate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
SCYSJFKWFQZRJW-UHFFFAOYSA-N 4-chloro-3-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC(C(Cl)=O)=CC=C1Cl SCYSJFKWFQZRJW-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
241000700159 Rattus Species 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000001631 hypertensive effect Effects 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
239000010410 layer Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000155 melt Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
235000011118 potassium hydroxide Nutrition 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
MHRDCHHESNJQIS-GSVOUGTGSA-N (2s)-2-methyl-3-sulfanylpropanoic acid Chemical compound SC[C@@H](C)C(O)=O MHRDCHHESNJQIS-GSVOUGTGSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
NRPQRTKZKJQNKM-UHFFFAOYSA-N 4-chloro-3-sulfamoylbenzenecarbothioic s-acid Chemical compound NS(=O)(=O)C1=CC(C(S)=O)=CC=C1Cl NRPQRTKZKJQNKM-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
208000007530 Essential hypertension Diseases 0.000 description 1
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 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
DZLNHFMRPBPULJ-VKHMYHEASA-N L-thioproline Chemical compound OC(=O)[C@@H]1CSCN1 DZLNHFMRPBPULJ-VKHMYHEASA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
WGCOQYDRMPFAMN-ZDUSSCGKSA-N [(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-pyrimidin-5-ylmethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1C=NC=NC=1 WGCOQYDRMPFAMN-ZDUSSCGKSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
125000000637 arginyl group Chemical class N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 1
230000037396 body weight Effects 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
150000002332 glycine derivatives Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
201000005857 malignant hypertension Diseases 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
OTZHILQUNJIBCW-UHFFFAOYSA-M potassium;4-chloro-3-sulfamoylthiobenzate Chemical compound [K+].NS(=O)(=O)C1=CC(C([O-])=S)=CC=C1Cl OTZHILQUNJIBCW-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
206010038464 renal hypertension Diseases 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000005245 sintering Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Pyrrole Compounds (AREA)
Peptides Or Proteins (AREA)
Plural Heterocyclic Compounds (AREA)

NL7920076A 1978-10-05 1979-09-28 Cyclische iminocarbonzuurderivaten. NL7920076A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP53123189A JPS5829950B2 (ja)	1978-10-05	1978-10-05	環状イミノカルボン酸誘導体およびその塩類
JP12318978		1978-10-05

Publications (1)

Publication Number	Publication Date
NL7920076A true NL7920076A (nl)	1980-08-29

Family

ID=14854386

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7920076A NL7920076A (nl)	1978-10-05	1979-09-28	Cyclische iminocarbonzuurderivaten.

Country Status (10)

Country	Link
US (1)	US4450275A (fr)
JP (1)	JPS5829950B2 (fr)
BE (1)	BE879158A (fr)
ES (1)	ES484679A1 (fr)
FR (1)	FR2438036A1 (fr)
GB (1)	GB2045249B (fr)
IT (1)	IT1121045B (fr)
NL (1)	NL7920076A (fr)
SE (1)	SE434264B (fr)
WO (1)	WO1980000700A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4483861A (en) *	1978-10-31	1984-11-20	Santen Pharmaceutical Co., Ltd.	Antihypertensive sulfur-containing compounds
US4312990A (en)	1980-09-11	1982-01-26	E. R. Squibb & Sons, Inc.	1-Mercaptoacyl-3-[(aminosulfonyl) phenyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid
US4312809A (en)	1980-10-31	1982-01-26	E. R. Squibb & Sons, Inc.	Lactam derivatives of mercaptoacylamino acids
JPS57112381A (en) *	1980-12-29	1982-07-13	Santen Pharmaceut Co Ltd	Five-membered heterocyclic compound
US4681886A (en) *	1982-04-30	1987-07-21	E. R. Squibb & Sons, Inc.	Substituted 4-phenoxy or 4-phenylthio prolines
US4661515A (en) *	1982-07-21	1987-04-28	Usv Pharmaceutical Corporation	Compounds having angiotensin converting enzyme inhibitory activity and diuretic activity
US4536501A (en) *	1984-03-30	1985-08-20	E. R. Squibb & Sons, Inc.	Substituted 4-phenoxy or 4-phenylthio prolines
EP0190852A3 (fr) *	1985-01-31	1988-11-02	Ajinomoto Co., Inc.	Dérivés dipeptides et les médicaments antihypertensifs les contenant
US7056935B2 (en)	1995-06-07	2006-06-06	Gpi Nil Holdings, Inc.	Rotamase enzyme activity inhibitors
DE10115938A1 (de) *	2001-03-30	2002-10-10	Medigene Ag Ges Fuer Molekular	Verfahren zur Herstellung von Oxirancarbonsäuren und Derivaten davon

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4105776A (en) *	1976-06-21	1978-08-08	E. R. Squibb & Sons, Inc.	Proline derivatives and related compounds
US4046889A (en) *	1976-02-13	1977-09-06	E. R. Squibb & Sons, Inc.	Azetidine-2-carboxylic acid derivatives
AU518147B2 (en) *	1976-12-03	1981-09-17	E.R. Squibb & Sons, Inc.	Derivatives of thiazolidine, thiazine and morpholine carboxylic acids
US4192878A (en) *	1976-12-03	1980-03-11	E. R. Squibb & Sons, Inc.	Derivatives of thiazolidinecarboxylic acids and related acids
US4108886A (en) *	1977-03-11	1978-08-22	E. R. Squibb & Sons, Inc.	Thiopropanoylamino acid derivatives
FR2404635A1 (fr) *	1977-09-28	1979-04-27	Science Union & Cie	Nouveaux thioproprionylamides, leurs procedures d'obtention et leur emploi en therapeutique
IT7851510A0 (it) *	1977-10-28	1978-10-16	Sandoz Ag	Ammidi di amminoacidi ciclici loro preparazione e loro applicazione quali medicamenti
CA1120400A (fr) *	1977-12-27	1982-03-23	Zola P. Horovitz	Traitement de l'hypertension et medicaments utilises a cette fin
US4282235A (en) *	1978-05-22	1981-08-04	E. R. Squibb & Sons, Inc.	Derivatives of thiazolidinecarboxylic acids and related acids

1978
- 1978-10-05 JP JP53123189A patent/JPS5829950B2/ja not_active Expired
1979
- 1979-09-28 GB GB8017628A patent/GB2045249B/en not_active Expired
- 1979-09-28 NL NL7920076A patent/NL7920076A/nl not_active Application Discontinuation
- 1979-09-28 WO PCT/JP1979/000249 patent/WO1980000700A1/fr not_active Ceased
- 1979-10-03 BE BE2/58115A patent/BE879158A/fr not_active IP Right Cessation
- 1979-10-03 ES ES484679A patent/ES484679A1/es not_active Expired
- 1979-10-04 IT IT68916/79A patent/IT1121045B/it active
- 1979-10-04 FR FR7924683A patent/FR2438036A1/fr active Granted
1980
- 1980-06-04 SE SE8004166A patent/SE434264B/sv unknown
- 1980-09-28 US US06/227,104 patent/US4450275A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPS5549352A (en)	1980-04-09
BE879158A (fr)	1980-02-01
FR2438036A1 (fr)	1980-04-30
WO1980000700A1 (fr)	1980-04-17
ES484679A1 (es)	1980-05-16
IT7968916A0 (it)	1979-10-04
US4450275A (en)	1984-05-22
SE434264B (sv)	1984-07-16
GB2045249B (en)	1983-01-26
SE8004166L (sv)	1980-06-04
GB2045249A (en)	1980-10-29
IT1121045B (it)	1986-03-26
FR2438036B1 (fr)	1983-03-18
JPS5829950B2 (ja)	1983-06-25

Legal Events

Date	Code	Title
1980-09-10	A1A	A request for search or an international-type search has been filed
1980-09-25	BB	A search report has been drawn up
1980-11-25	BC	A request for examination has been filed
1985-01-01	A85	Still pending on 85-01-01
1986-05-01	BV	The patent application has lapsed

Publication	Publication Date	Title
Kubo et al.	1993	Nonpeptide angiotensin II receptor antagonists. Synthesis and biological activity of potential prodrugs of benzimidazole-7-carboxylic acids
EP0182165A1 (fr)	1986-05-28	Dérivés de thiényl de pyrazoles condensés
KR960010346B1 (ko)	1996-07-30	4(3h)-퀴나졸리논 유도체, 이의 제조방법 및 약제학적 조성물
KR940009528B1 (ko)	1994-10-14	헤테로 고리 화합물의 제조 방법
EP0097821B1 (fr)	1988-07-13	Dihydropyridines douées d'une activité antagoniste pour le calcium, leur procédé de préparation et leur application dans des compositions pharmaceutiques
US3705153A (en)	1972-12-05	Novel thiazolyacetic acids and salts thereof
US4450275A (en)	1984-05-22	Cyclic iminocarboxylic acid derivatives
SI9200240A (en)	1993-06-30	New acylates from imidazole-5-carboxylic acid derivatives and process for their preparation and their use
Atwal et al.	1992	Dihydropyrimidine angiotensin II receptor antagonists
EP0299493B1 (fr)	1994-06-08	N-[(2-oxopyrrolidin-1-yl)acétyl]pipérazines et médicament contre la démence sénile
CA1271751A (fr)	1990-07-17	Derives de dihydro-imidazo[1,2-a]pyrimidine
DeWald et al.	1988	Synthesis and Potential Antipsychotic Activity of 1H-Imidazo [1, 2-c] pyrazolo [3, 4-e] pyrimidines
WO1997030029A1 (fr)	1997-08-21	Procede de preparation de derives (prodigiosines) de 2,2'-bipyrrolyl-pyrromethene
Takada et al.	1988	Thienylpyrazoloquinolines: potent agonists and inverse agonists to benzodiazepine receptors
US4436746A (en)	1984-03-13	Thromboxane synthetase inhibitory N-substituted-2-(1-imidazolyl)indoles
SE434836B (sv)	1984-08-20	Tiazolidinforeningar
US5326879A (en)	1994-07-05	Indole derivatives
HU198048B (en)	1989-07-28	Process for production of derivatives of imidazo-piridine and medical preparatives containing these substances
US4460777A (en)	1984-07-17	N-Substituted-2-pyridylindoles
EP0329126B1 (fr)	1994-08-10	Composés hétérocycliques et agents antiulcéreux
NL8003803A (nl)	1981-01-06	Nieuwe zwavelhoudende isochinolinederivaten, deze ver- binding bevattende farmaceutische preparaten en werkwijze voor de bereiding van deze nieuwe ver- bindingen.
Marsham et al.	1991	Quinazoline antifolate thymidylate synthase inhibitors: bridge modifications and conformationally restricted analogs in the C2-methyl series
KR20150098614A (ko)	2015-08-28	신규 벤조아제핀 유도체 및 그 의약 용도
US6127362A (en)	2000-10-03	9,10-diazatricyclo[4,4,1,12,5 ] decane and 2,7-diazatricyclo [4,4,0,03,8 ] decane derivatives having analgesic activity
DK168953B1 (da)	1994-07-18	5- eller 6-benzyloxysubstituerede beta-carbolin-3-carboxylsyreestere samt fremgangsmåde til fremstilling heraf