SU1115668A3 - Способ получени производных пролина - Google Patents

Способ получени производных пролина Download PDF

Info

Publication number: SU1115668A3
Authority: SU; USSR - Soviet Union
Prior art keywords: solution; proline; general formula; mol; salt
Prior art date: 1978-12-22

Application number

SU792860149A

Other languages

English (en)

Russian (ru)

Inventor

Кранчо Джон

Original Assignee

Е.Р.Сквибб Энд Санз,Инк (Фирма)

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.)

1978-12-22

Filing date

1979-12-21

Publication date

1984-09-23

1979-12-21 Application filed by Е.Р.Сквибб Энд Санз,Инк (Фирма) filed Critical Е.Р.Сквибб Энд Санз,Инк (Фирма)

1984-09-23 Application granted granted Critical

1984-09-23 Publication of SU1115668A3 publication Critical patent/SU1115668A3/ru

Links

150000003147 proline derivatives Chemical class 0.000 title claims 3
238000004519 manufacturing process Methods 0.000 title claims 2
-1 polymethylene chain Polymers 0.000 claims abstract description 33
150000001875 compounds Chemical class 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 6
125000001589 carboacyl group Chemical group 0.000 claims abstract description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052740 iodine Inorganic materials 0.000 claims abstract description 4
239000011630 iodine Substances 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
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 claims abstract description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
239000001301 oxygen Substances 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
239000011593 sulfur Substances 0.000 claims abstract description 3
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims abstract 4
150000002431 hydrogen Chemical class 0.000 claims abstract 2
238000002955 isolation Methods 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
238000000034 method Methods 0.000 abstract description 6
238000000926 separation method Methods 0.000 abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 96
239000000243 solution Substances 0.000 description 72
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
150000003839 salts Chemical class 0.000 description 43
229960002429 proline Drugs 0.000 description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
239000002904 solvent Substances 0.000 description 29
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
239000010410 layer Substances 0.000 description 27
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 21
239000000047 product Substances 0.000 description 19
239000007787 solid Substances 0.000 description 19
239000008346 aqueous phase Substances 0.000 description 17
238000001816 cooling Methods 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
239000003921 oil Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000002253 acid Substances 0.000 description 15
229910052943 magnesium sulfate Inorganic materials 0.000 description 15
235000019341 magnesium sulphate Nutrition 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
229910052786 argon Inorganic materials 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
KUSYIGBGHPOWEL-UHFFFAOYSA-N 2-methyl nonaoic acid Chemical compound CCCCCCCC(C)C(O)=O KUSYIGBGHPOWEL-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
239000000463 material Substances 0.000 description 9
239000003054 catalyst Substances 0.000 description 7
238000000921 elemental analysis Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000006188 syrup Substances 0.000 description 7
235000020357 syrup Nutrition 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
150000003946 cyclohexylamines Chemical class 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
239000000126 substance Substances 0.000 description 5
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229910000343 potassium bisulfate Inorganic materials 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
238000005303 weighing Methods 0.000 description 4
YRCGAHTZOXPQPR-UHFFFAOYSA-N 2-ethylnonanoic acid Chemical compound CCCCCCCC(CC)C(O)=O YRCGAHTZOXPQPR-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
102000015427 Angiotensins Human genes 0.000 description 3
108010064733 Angiotensins Proteins 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
206010020772 Hypertension Diseases 0.000 description 3
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 3
241000700159 Rattus Species 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 3
229960000830 captopril Drugs 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
238000010899 nucleation Methods 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
102000005862 Angiotensin II Human genes 0.000 description 2
101800000733 Angiotensin-2 Proteins 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
206010020852 Hypertonia Diseases 0.000 description 2
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 2
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229950006323 angiotensin ii Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000012071 phase Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000005245 sintering Methods 0.000 description 2
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 2
229910001948 sodium oxide Inorganic materials 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
FQBKUPURMALCOI-WCCKRBBISA-N (2S)-pyrrolidine-2-carboxylic acid hydrobromide Chemical compound Br.OC(=O)[C@@H]1CCCN1 FQBKUPURMALCOI-WCCKRBBISA-N 0.000 description 1
JXGVXCZADZNAMJ-NSHDSACASA-N (2s)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)OCC1=CC=CC=C1 JXGVXCZADZNAMJ-NSHDSACASA-N 0.000 description 1
RPLLCMZOIFOBIF-NSHDSACASA-N (2s)-4-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CC(=O)CN1C(=O)OCC1=CC=CC=C1 RPLLCMZOIFOBIF-NSHDSACASA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
OVXWHHYDMKASOR-UHFFFAOYSA-N 1-methylcyclohexa-2,4-diene-1-sulfonic acid Chemical compound OS(=O)(=O)C1(C)CC=CC=C1 OVXWHHYDMKASOR-UHFFFAOYSA-N 0.000 description 1
YHYNXECYFYSAGK-UHFFFAOYSA-N 2-acetylsulfanyl-3,3,3-trifluoro-2-methylpropanoic acid Chemical compound CC(=O)SC(C)(C(O)=O)C(F)(F)F YHYNXECYFYSAGK-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
244000099147 Ananas comosus Species 0.000 description 1
235000007119 Ananas comosus Nutrition 0.000 description 1
101800000734 Angiotensin-1 Proteins 0.000 description 1
102400000344 Angiotensin-1 Human genes 0.000 description 1
102000004881 Angiotensinogen Human genes 0.000 description 1
108090001067 Angiotensinogen Proteins 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
241001609030 Brosme brosme Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
241000243251 Hydra Species 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
241000406668 Loxodonta cyclotis Species 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
101100518501 Mus musculus Spp1 gene Proteins 0.000 description 1
101100409308 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) adv-1 gene Proteins 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
241001442654 Percnon planissimum Species 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
235000014676 Phragmites communis Nutrition 0.000 description 1
108090000783 Renin Proteins 0.000 description 1
102000005686 Serum Globulins Human genes 0.000 description 1
108010045362 Serum Globulins Proteins 0.000 description 1
101100117436 Thermus aquaticus polA gene Proteins 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
HUMHYXGDUOGHTG-HEZXSMHISA-N alpha-D-GalpNAc-(1->3)-[alpha-L-Fucp-(1->2)]-D-Galp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@@H](CO)OC1O HUMHYXGDUOGHTG-HEZXSMHISA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 1
239000002416 angiotensin derivative Substances 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
150000001844 chromium Chemical class 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
231100000676 disease causative agent Toxicity 0.000 description 1
239000003814 drug Substances 0.000 description 1
JTRONPPAUSSTQI-UHFFFAOYSA-N ethane-1,2-diol;ethanol Chemical compound CCO.OCCO JTRONPPAUSSTQI-UHFFFAOYSA-N 0.000 description 1
DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
229960002591 hydroxyproline Drugs 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
238000003475 lamination Methods 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
229940092597 prolia Drugs 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000007670 refining Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical class [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002594 sorbent Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
230000002792 vascular Effects 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
230000002618 waking effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/10—Spiro-condensed systems
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Peptides Or Proteins (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Compositions Of Macromolecular Compounds (AREA)

SU792860149A 1978-12-22 1979-12-21 Способ получени производных пролина SU1115668A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US97231478A	1978-12-22	1978-12-22

Publications (1)

Publication Number	Publication Date
SU1115668A3 true SU1115668A3 (ru)	1984-09-23

Family

ID=25519507

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU792860149A SU1115668A3 (ru)	1978-12-22	1979-12-21	Способ получени производных пролина

Country Status (31)

Country	Link
JP (1)	JPS5594357A (xx)
AT (1)	AT374174B (xx)
AU (1)	AU533149B2 (xx)
BE (1)	BE880815A (xx)
CA (1)	CA1132985A (xx)
CH (1)	CH642065A5 (xx)
CS (1)	CS215036B2 (xx)
DD (1)	DD148338A5 (xx)
DE (1)	DE2951200A1 (xx)
DK (1)	DK159115C (xx)
ES (2)	ES487180A0 (xx)
FI (1)	FI70886C (xx)
FR (1)	FR2444669A1 (xx)
GB (1)	GB2039478B (xx)
GR (1)	GR78384B (xx)
HK (1)	HK15684A (xx)
HU (1)	HU179644B (xx)
IE (1)	IE49321B1 (xx)
IL (1)	IL58930A (xx)
IT (1)	IT1126841B (xx)
LU (1)	LU82023A1 (xx)
NL (1)	NL7909246A (xx)
NO (1)	NO153569C (xx)
NZ (1)	NZ192449A (xx)
PH (1)	PH19213A (xx)
PL (1)	PL133414B1 (xx)
PT (1)	PT70620A (xx)
SE (1)	SE451839B (xx)
SU (1)	SU1115668A3 (xx)
YU (1)	YU314879A (xx)
ZA (1)	ZA796720B (xx)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2455585A1 (fr) *	1979-05-04	1980-11-28	Ono Pharmaceutical Co	Derives d'oxoaminoacides, procede de fabrication et composition pharmaceutique
US4288368A (en) *	1979-07-30	1981-09-08	E. R. Squibb & Sons, Inc.	Dithioacylproline derivatives
US4291040A (en) *	1979-10-22	1981-09-22	E. R. Squibb & Sons, Inc.	Mercaptoacyl derivatives of 4-disubstituted prolines and 4-substituted dehydroprolines
US4356182A (en) *	1979-10-22	1982-10-26	E. R. Squibb & Sons, Inc.	Mercaptoacyl derivatives of 4-disubstituted prolines
HU184082B (en) *	1979-12-29	1984-06-28	Egyt Gyogyszervegyeszeti Gyar	Process for preparing 1-3-/3mercapto-/2s/-methyl-propinyl/-pyrrolidine-/2s/-carboxylic acid
US4284624A (en)	1980-05-02	1981-08-18	E. R. Squibb & Sons, Inc.	Mixed disulfides
US4316905A (en) *	1980-07-01	1982-02-23	E. R. Squibb & Sons, Inc.	Mercaptoacyl derivatives of various 4-substituted prolines
US4311705A (en) *	1980-10-06	1982-01-19	E. R. Squibb & Sons, Inc.	Carboxyalkanoyl and hydroxycarbamoylalkanoyl derivatives of substituted prolines
US4462943A (en) *	1980-11-24	1984-07-31	E. R. Squibb & Sons, Inc.	Carboxyalkyl amino acid derivatives of various substituted prolines
US4416831A (en)	1981-04-27	1983-11-22	E. R. Squibb & Sons, Inc.	Amino and substituted amino phosphinylalkanoyl compounds
US4374131A (en)	1981-04-27	1983-02-15	E. R. Squibb & Sons, Inc.	Amino and substituted amino phosphinyl-alkanoyl compounds
US4381297A (en)	1981-05-04	1983-04-26	E. R. Squibb & Sons, Inc.	Substituted carbonyl phosphinyl-alkanoyl compounds
US4416833A (en)	1981-05-04	1983-11-22	E. R. Squibb & Sons, Inc.	Substituted carbonyl phosphinyl-alkanoyl compounds
US4555506A (en) *	1981-12-24	1985-11-26	E. R. Squibb & Sons, Inc.	Phosphorus containing compounds and use as hypotensives
US4560680A (en) *	1982-03-15	1985-12-24	E. R. Squibb & Sons, Inc.	Aminoalkyl and related substituted phosphinic acid angiotensin converting enzyme inhibitors
US4452791A (en) *	1982-03-15	1984-06-05	E. R. Squibb & Sons, Inc.	Aminoalkyl and related substituted phosphinic acid angiotensin converting enzyme inhibitors
ZA832762B (en) *	1982-04-30	1983-12-28	Squibb & Sons Inc	Substituted 4-phenoxy prolines
US4452790A (en) *	1982-06-23	1984-06-05	E. R. Squibb & Sons, Inc.	Phosphonyl hydroxyacyl amino acid derivatives as antihypertensives
US4703043A (en) *	1982-06-23	1987-10-27	E. R. Squibb & Sons, Inc.	Phosphonyl hydroxyacyl amino acid derivatives as antihypertensive
US4616005A (en) *	1982-06-23	1986-10-07	E. R. Squibb & Sons, Inc.	Phosphonyl hydroxyacyl amino acid derivatives as antihypertensives
US4567166A (en) *	1982-07-14	1986-01-28	E. R. Squibb & Sons, Inc.	Amino and substituted amino phosphinylalkanoyl compounds useful for treating hypertension
US4709046A (en) *	1983-05-09	1987-11-24	E. R. Squibb & Sons, Inc.	Acylmercaptoalkanoyl and mercaptoalkanoyl spiro compounds
CA2021409A1 (en) *	1989-08-21	1991-02-22	Donald S. Karanewsky	Phosphonate substituted amino or imino acids useful as antihypertensives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4046889A (en) *	1976-02-13	1977-09-06	E. R. Squibb & Sons, Inc.	Azetidine-2-carboxylic acid derivatives
US4091024A (en) *	1976-12-03	1978-05-23	E. R. Squibb & Sons, Inc.	Pyrrolidine and piperidine-2-carboxylic acid derivatives
IT7851510A0 (it) *	1977-10-28	1978-10-16	Sandoz Ag	Ammidi di amminoacidi ciclici loro preparazione e loro applicazione quali medicamenti
PH15381A (en) *	1978-02-21	1982-12-17	Squibb & Sons Inc	Halogen substituted mercaptoacylamino acids
CA1144930A (en) *	1978-08-11	1983-04-19	Miguel A. Ondetti	Mercaptoacyl derivatives of substituted prolines

1979
- 1979-12-07 CA CA341,486A patent/CA1132985A/en not_active Expired
- 1979-12-11 AU AU53714/79A patent/AU533149B2/en not_active Ceased
- 1979-12-11 ZA ZA00796720A patent/ZA796720B/xx unknown
- 1979-12-12 IL IL58930A patent/IL58930A/xx unknown
- 1979-12-13 GB GB7942991A patent/GB2039478B/en not_active Expired
- 1979-12-13 GR GR60746A patent/GR78384B/el unknown
- 1979-12-17 CS CS798891A patent/CS215036B2/cs unknown
- 1979-12-18 NZ NZ192449A patent/NZ192449A/en unknown
- 1979-12-19 NO NO794181A patent/NO153569C/no unknown
- 1979-12-19 FR FR7931132A patent/FR2444669A1/fr active Granted
- 1979-12-19 IE IE2468/79A patent/IE49321B1/en unknown
- 1979-12-19 PH PH23434A patent/PH19213A/en unknown
- 1979-12-19 DE DE19792951200 patent/DE2951200A1/de not_active Ceased
- 1979-12-20 AT AT0805479A patent/AT374174B/de active
- 1979-12-20 CH CH1133979A patent/CH642065A5/de not_active IP Right Cessation
- 1979-12-20 SE SE7910550A patent/SE451839B/sv not_active IP Right Cessation
- 1979-12-21 PL PL1979220609A patent/PL133414B1/pl unknown
- 1979-12-21 NL NL7909246A patent/NL7909246A/nl not_active Application Discontinuation
- 1979-12-21 HU HU79SU1047A patent/HU179644B/hu not_active IP Right Cessation
- 1979-12-21 FI FI794027A patent/FI70886C/fi not_active IP Right Cessation
- 1979-12-21 LU LU82023A patent/LU82023A1/de unknown
- 1979-12-21 YU YU03148/79A patent/YU314879A/xx unknown
- 1979-12-21 BE BE0/198709A patent/BE880815A/fr not_active IP Right Cessation
- 1979-12-21 ES ES487180A patent/ES487180A0/es active Granted
- 1979-12-21 PT PT70620A patent/PT70620A/pt unknown
- 1979-12-21 DK DK550079A patent/DK159115C/da not_active IP Right Cessation
- 1979-12-21 DD DD79218061A patent/DD148338A5/de not_active IP Right Cessation
- 1979-12-21 IT IT51167/79A patent/IT1126841B/it active
- 1979-12-21 SU SU792860149A patent/SU1115668A3/ru active
- 1979-12-22 JP JP16747179A patent/JPS5594357A/ja active Pending
1980
- 1980-02-20 ES ES488752A patent/ES8103039A1/es not_active Expired
1984
- 1984-02-23 HK HK156/84A patent/HK15684A/xx unknown

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
1. Вейганд-Хильчетаг. Методы эксперимента в органической химии, М,, Хими , 1968, с. 431. 2. Патент СССР № 747422, кл. С 07 D 207/16, 1976. *

Also Published As

Publication number	Publication date
IT1126841B (it)	1986-05-21
DD148338A5 (de)	1981-05-20
FR2444669B1 (xx)	1983-06-03
FI70886C (fi)	1986-10-27
IL58930A (en)	1983-07-31
ES8102094A1 (es)	1980-12-16
FI794027A7 (fi)	1980-06-23
YU314879A (en)	1983-04-30
AU533149B2 (en)	1983-11-03
NO153569B (no)	1986-01-06
GB2039478A (en)	1980-08-13
IE792468L (en)	1980-06-22
ZA796720B (en)	1980-11-26
ES487180A0 (es)	1980-12-16
HK15684A (en)	1984-03-02
NZ192449A (en)	1984-05-31
BE880815A (fr)	1980-06-23
NO153569C (no)	1986-05-21
JPS5594357A (en)	1980-07-17
CA1132985A (en)	1982-10-05
DK159115B (da)	1990-09-03
IE49321B1 (en)	1985-09-18
ES488752A0 (es)	1981-02-16
DK550079A (da)	1980-06-23
NL7909246A (nl)	1980-06-24
CS215036B2 (en)	1982-06-25
FR2444669A1 (fr)	1980-07-18
PL220609A1 (xx)	1980-12-01
NO794181L (no)	1980-06-24
GR78384B (xx)	1984-09-26
ATA805479A (de)	1983-08-15
GB2039478B (en)	1983-02-16
AU5371479A (en)	1980-06-26
DK159115C (da)	1991-02-11
PL133414B1 (en)	1985-05-31
SE7910550L (sv)	1980-06-23
PT70620A (en)	1980-01-01
IT7951167A0 (it)	1979-12-21
DE2951200A1 (de)	1980-07-10
CH642065A5 (de)	1984-03-30
PH19213A (en)	1986-02-04
ES8103039A1 (es)	1981-02-16
AT374174B (de)	1984-03-26
FI70886B (fi)	1986-07-18
HU179644B (en)	1982-11-29
SE451839B (sv)	1987-11-02
IL58930A0 (en)	1980-03-31
LU82023A1 (de)	1980-04-23

Publication	Publication Date	Title
SU1115668A3 (ru)	1984-09-23	Способ получени производных пролина
Clarke et al.	1973	Compounds affecting the central nervous system. 4. 3. beta.-phenyltropane-2-carboxylic esters and analogs
EP0072352B1 (de)	1986-03-05	Benzazepin-2-one, Verfahren zu ihrer Herstellung, pharmazeutische Präparate die diese Verbindungen enthalten, sowie die Verbindungen zur therapeutischen Verwendung
DE69822839T2 (de)	2004-08-19	Derivate von aryloxyarylsulfonylamino hydroxyaminsäuren
DE69716619T2 (de)	2003-06-26	Phosphinsäureamide als matrix metalloprotease inhibitoren
EP0046953B1 (de)	1989-12-06	Aminosäurederivate, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung
EP0119954B1 (de)	1990-03-14	Gewisse 3-Amino-1-benzazepin-2-on-1-alkansäuren, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie ihre therapeutische Verwendung
DE69716934T2 (de)	2003-07-31	1,3-diheterozyklische metalloprotease inhibitoren
EP0119161B1 (de)	1989-06-28	Gewisse Benzazocinon- und Benzazoninon-Derivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie ihre therapeutische Verwendung
Fleet et al.	1988	Synthesis from D-mannose of 1, 4-dideoxy-1, 4-imino-L-ribitol and of the α-mannosidase inhibitor 1, 4-dideoxy-1, 4-imino-D-talitol
EP0074070A1 (de)	1983-03-16	Harnstoffderivate, Verfahren zu ihrer Herstellung und diese enthaltende Medikamente sowie deren Verwendung
DD201787A5 (de)	1983-08-10	Verfahren zur herstellung von substituierten acylderivaten von 1,2,3,4-tetrahydroisochinolin-3-carbonsaeuren
DE69730033T2 (de)	2005-07-21	Spirocyclisch metalloprotease inhibitoren
JPS6056705B2 (ja)	1985-12-11	プロリン誘導体および関連化合物の製造法
US6187782B1 (en)	2001-02-13	Morphinane derivatives and medicinal use thereof
JP2001527058A (ja)	2001-12-25	ノイラミニダーゼ阻害剤として有用な置換シクロペンタン及びシクロペンテン化合物
JPS58150547A (ja)	1983-09-07	アミノ酸誘導体とその医療への応用
KR100220879B1 (ko)	2000-03-15	안지오텐신 전환 효소 억제제로서 유용한 신규 아미노 및 니트로 함유 트리시클릭 화합물
SK20199A3 (en)	2000-03-13	Ether muscarinic antagonists
EP0204349A2 (de)	1986-12-10	Neue heteroaromatische Aminderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
RU2346933C2 (ru)	2009-02-20	Соединение, обладающее действием против hcv, и способ его получения
EP1055683A1 (en)	2000-11-29	Novel acetamide derivative and use thereof
EP0282898A2 (de)	1988-09-21	Propiolophenonderivate
JPH07505120A (ja)	1995-06-08	チアフィゾベニンのカルバミン酸類縁化合物、医薬品用組成物、ならびにコリンエステラーゼ阻害方法
EP0093805A1 (en)	1983-11-16	Octahydro-2-(omega-mercaptoalkanoyl)3-oxo-1H-isoindole-1-carboxylic acids and esters