JPH0134987B2 - - Google Patents

Info

Publication number: JPH0134987B2
Authority: JP; Japan
Prior art keywords: proline; compound according; methyl; hydrogen; oxopropyl
Prior art date: 1978-08-11
Legal status (The legal status 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 status listed.): Expired

Application number

JP54102722A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5527199A (en

Inventor

Enjeru Ondetsutei Miigeru

Kurapucho Jon

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ER Squibb and Sons LLC

Original Assignee

ER Squibb and Sons LLC

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.)

1978-08-11

Filing date

1979-08-10

Publication date

1989-07-21

1979-08-10 Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC

1980-02-27 Publication of JPS5527199A publication Critical patent/JPS5527199A/ja

1989-07-21 Publication of JPH0134987B2 publication Critical patent/JPH0134987B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 82
229960002429 proline Drugs 0.000 claims description 53
239000001257 hydrogen Substances 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 41
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 29
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical group OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 26
-1 3-mercapto-1-oxopropyl Chemical group 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
229910052717 sulfur Chemical group 0.000 claims description 8
229930182821 L-proline Natural products 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
150000001447 alkali salts Chemical class 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims 6
150000001721 carbon Chemical group 0.000 claims 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 147
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 93
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
239000000243 solution Substances 0.000 description 64
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
238000004519 manufacturing process Methods 0.000 description 37
239000000203 mixture Substances 0.000 description 34
239000000047 product Substances 0.000 description 32
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 31
239000010410 layer Substances 0.000 description 31
238000002844 melting Methods 0.000 description 31
230000008018 melting Effects 0.000 description 31
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
235000013930 proline Nutrition 0.000 description 26
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
238000000034 method Methods 0.000 description 22
239000002253 acid Substances 0.000 description 21
238000003756 stirring Methods 0.000 description 21
239000007787 solid Substances 0.000 description 19
239000002904 solvent Substances 0.000 description 19
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000012044 organic layer Substances 0.000 description 15
238000002360 preparation method Methods 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
238000000921 elemental analysis Methods 0.000 description 14
239000000126 substance Substances 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
239000007858 starting material Substances 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
238000005245 sintering Methods 0.000 description 11
229910000029 sodium carbonate Inorganic materials 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
239000012300 argon atmosphere Substances 0.000 description 10
239000000463 material Substances 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
238000001816 cooling Methods 0.000 description 9
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 9
229910000343 potassium bisulfate Inorganic materials 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 8
150000003946 cyclohexylamines Chemical class 0.000 description 8
239000000284 extract Substances 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
RNXKXUOGQKYKTH-UHNVWZDZSA-N (2s,4r)-4-methoxypyrrolidine-2-carboxylic acid Chemical compound CO[C@H]1CN[C@H](C(O)=O)C1 RNXKXUOGQKYKTH-UHNVWZDZSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
102000015427 Angiotensins Human genes 0.000 description 6
108010064733 Angiotensins Proteins 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000002585 base Substances 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
239000003814 drug Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
RNXKXUOGQKYKTH-WHFBIAKZSA-N (2s,4s)-4-methoxypyrrolidine-2-carboxylic acid Chemical compound CO[C@@H]1CN[C@H](C(O)=O)C1 RNXKXUOGQKYKTH-WHFBIAKZSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
229910001923 silver oxide Inorganic materials 0.000 description 5
239000012265 solid product Substances 0.000 description 5
239000006188 syrup Substances 0.000 description 5
235000020357 syrup Nutrition 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
238000005406 washing Methods 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000036772 blood pressure Effects 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
150000003568 thioethers Chemical class 0.000 description 4
SRQAKAAEVLROCY-RYUDHWBXSA-N (2s,4s)-4-methoxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](OC)C[C@@H](C(O)=O)N1C(=O)OCC1=CC=CC=C1 SRQAKAAEVLROCY-RYUDHWBXSA-N 0.000 description 3
206010020772 Hypertension Diseases 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 3
YEESUBCSWGVPCE-UHFFFAOYSA-N azanylidyneoxidanium iron(2+) pentacyanide Chemical compound [Fe++].[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.N#[O+] YEESUBCSWGVPCE-UHFFFAOYSA-N 0.000 description 3
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229960002460 nitroprusside Drugs 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
OAOSKXATXOABJJ-HTRCEHHLSA-N (2R,3R)-3-methyl-1-(3-sulfanylpropanoyl)pyrrolidine-2-carbothioic S-acid Chemical compound SCCC(=O)N1[C@@H](C(=S)O)[C@@H](CC1)C OAOSKXATXOABJJ-HTRCEHHLSA-N 0.000 description 2
JMAXYNGGIHCBIV-RFZPGFLSSA-N (2R,3R)-3-methylpyrrolidine-2-carbothioic S-acid Chemical compound C[C@H]1[C@@H](NCC1)C(=S)O JMAXYNGGIHCBIV-RFZPGFLSSA-N 0.000 description 2
NVQQVSZPBANGFD-UWVGGRQHSA-N (2s,4s)-4-(4-fluorophenoxy)pyrrolidine-2-carboxylic acid Chemical compound C1N[C@H](C(=O)O)C[C@@H]1OC1=CC=C(F)C=C1 NVQQVSZPBANGFD-UWVGGRQHSA-N 0.000 description 2
WWVCWLBEARZMAH-QWRGUYRKSA-N (2s,4s)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](O)C[C@@H](C(O)=O)N1C(=O)OCC1=CC=CC=C1 WWVCWLBEARZMAH-QWRGUYRKSA-N 0.000 description 2
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 2
RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 2
UNUDUTMFKRKUIJ-UHFFFAOYSA-N 4-oxopentanethioyl chloride Chemical compound CC(=O)CCC(Cl)=S UNUDUTMFKRKUIJ-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
241000167854 Bourreria succulenta Species 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
239000003929 acidic solution Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
235000019693 cherries Nutrition 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 2
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
239000007789 gas Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
229960002591 hydroxyproline Drugs 0.000 description 2
150000002500 ions Chemical class 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
150000004702 methyl esters Chemical class 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
150000003148 prolines Chemical class 0.000 description 2
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 2
ZEERPIASPMMKRH-ZETCQYMHSA-N propyl (2s)-pyrrolidine-2-carboxylate Chemical compound CCCOC(=O)[C@@H]1CCCN1 ZEERPIASPMMKRH-ZETCQYMHSA-N 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 2
UGCIENQXZWUFRM-GMSGAONNSA-N (2R,3R)-1-(3-acetylsulfanylpropanoyl)-3-methylpyrrolidine-2-carbothioic S-acid Chemical compound C(C)(=O)SCCC(=O)N1[C@@H](C(=S)O)[C@@H](CC1)C UGCIENQXZWUFRM-GMSGAONNSA-N 0.000 description 1
ANUPMJRYMWYUEK-ZYHUDNBSSA-N (2R,3R)-3-methyl-1-phenylmethoxycarbonylpyrrolidine-2-carbothioic S-acid Chemical compound C(C1=CC=CC=C1)OC(=O)N1[C@@H](C(=S)O)[C@@H](CC1)C ANUPMJRYMWYUEK-ZYHUDNBSSA-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
MOEDDXVKEINTQF-BYPYZUCNSA-N (2s)-1-sulfanylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1S MOEDDXVKEINTQF-BYPYZUCNSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
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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
- C07D207/12—Oxygen or sulfur atoms
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- 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
- C07C327/00—Thiocarboxylic acids
- 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

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

JP10272279A 1978-08-11 1979-08-10 Mercaptoacylproline derivative and its manufacture and use Granted JPS5527199A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US93288378A	1978-08-11	1978-08-11
KR1019790002731A KR830002450B1 (ko)	1978-08-11	1979-08-10	치환 프로린의 메르캅토아실 유도체의 제조방법

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP63323204A Division JPH01287069A (ja)	1978-08-11	1988-12-21	メルカプトアシルプロリン誘導体の製法ならびに用途

Publications (2)

Publication Number	Publication Date
JPS5527199A JPS5527199A (en)	1980-02-27
JPH0134987B2 true JPH0134987B2 (ko)	1989-07-21

Family

ID=26626596

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP10272279A Granted JPS5527199A (en)	1978-08-11	1979-08-10	Mercaptoacylproline derivative and its manufacture and use
JP63323204A Pending JPH01287069A (ja)	1978-08-11	1988-12-21	メルカプトアシルプロリン誘導体の製法ならびに用途

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
JP63323204A Pending JPH01287069A (ja)	1978-08-11	1988-12-21	メルカプトアシルプロリン誘導体の製法ならびに用途

Country Status (30)

Country	Link
JP (2)	JPS5527199A (ko)
KR (1)	KR830002450B1 (ko)
AR (1)	AR229081A1 (ko)
AT (1)	AT379589B (ko)
AU (1)	AU530690B2 (ko)
BE (1)	BE878191A (ko)
CA (1)	CA1144930A (ko)
CH (1)	CH642064A5 (ko)
CS (1)	CS228118B2 (ko)
DD (1)	DD145749A5 (ko)
DE (1)	DE2932021C2 (ko)
DK (1)	DK154553C (ko)
ES (1)	ES483311A1 (ko)
FI (1)	FI69834C (ko)
FR (1)	FR2435469A1 (ko)
GB (1)	GB2028327B (ko)
GR (1)	GR72420B (ko)
IE (1)	IE48802B1 (ko)
IN (1)	IN152712B (ko)
IT (1)	IT1117782B (ko)
LU (2)	LU81593A1 (ko)
NL (2)	NL193374C (ko)
NZ (1)	NZ191036A (ko)
PH (1)	PH15030A (ko)
PT (1)	PT70049A (ko)
RO (1)	RO78870B (ko)
SE (1)	SE447477B (ko)
SU (1)	SU1066460A3 (ko)
YU (1)	YU41876B (ko)
ZA (1)	ZA793633B (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH05344844A (ja) *	1992-06-12	1993-12-27	Suzumo Kiko Kk	焼おむすびせんべいの製造方法

Families Citing this family (44)

* 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
CA1132985A (en) *	1978-12-22	1982-10-05	John Krapcho	Ketal and thioketal derivatives of mercaptoacyl prolines
US4347371A (en) *	1978-12-30	1982-08-31	Santen Pharmaceutical Co., Ltd.	Disulfide compounds
US4234489A (en) *	1979-06-25	1980-11-18	E. R. Squibb & Sons, Inc.	Pyroglutamic acid derivatives and analogs
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
US4692458A (en) *	1980-03-05	1987-09-08	University Of Miami	Anti-hypertensive agents
AU542211B2 (en) *	1980-03-07	1985-02-14	Gruppo Lepetit S.P.A.	Mercaptocycloalkyl carbonyl prolines
SE431331B (sv) *	1980-03-21	1984-01-30	Squibb & Sons Inc	Nya terapeutiskt aktiva svavelinnehallande n-acylerade derivat av 4-oxo-l-prolin
US4284624A (en)	1980-05-02	1981-08-18	E. R. Squibb & Sons, Inc.	Mixed disulfides
US4390695A (en) *	1980-06-23	1983-06-28	E. R. Squibb & Sons, Inc.	Imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids
US4578474A (en) *	1980-06-23	1986-03-25	E. R. Squibb & Sons, Inc.	Imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids
US4316905A (en) *	1980-07-01	1982-02-23	E. R. Squibb & Sons, Inc.	Mercaptoacyl derivatives of various 4-substituted prolines
US4332726A (en) *	1980-08-25	1982-06-01	E. R. Squibb & Sons, Inc.	Purification of mercaptoacyl amino acids
US4307110A (en) *	1980-09-12	1981-12-22	E. R. Squibb & Sons, Inc.	Mercaptoacyl derivatives of 3-substituted proline derivatives
US4311705A (en) *	1980-10-06	1982-01-19	E. R. Squibb & Sons, Inc.	Carboxyalkanoyl and hydroxycarbamoylalkanoyl derivatives of substituted prolines
US4312809A (en)	1980-10-31	1982-01-26	E. R. Squibb & Sons, Inc.	Lactam derivatives of mercaptoacylamino acids
US4462943A (en) *	1980-11-24	1984-07-31	E. R. Squibb & Sons, Inc.	Carboxyalkyl amino acid derivatives of various substituted prolines
US4337201A (en) *	1980-12-04	1982-06-29	E. R. Squibb & Sons, Inc.	Phosphinylalkanoyl substituted prolines
US4384123A (en) *	1980-12-04	1983-05-17	E. R. Squibb & Sons, Inc.	Phosphinylalkanoyl 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
US4416833A (en)	1981-05-04	1983-11-22	E. R. Squibb & Sons, Inc.	Substituted carbonyl phosphinyl-alkanoyl compounds
US4381297A (en)	1981-05-04	1983-04-26	E. R. Squibb & Sons, Inc.	Substituted carbonyl phosphinyl-alkanoyl compounds
US4497953A (en) *	1981-06-01	1985-02-05	E. R. Squibb & Sons, Inc.	Imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids
US4377701A (en) *	1981-09-21	1983-03-22	E. R. Squibb & Sons, Inc.	4-Methylene-1-[[(alranoyl or arylcarbonyl)mercapto]acyl]proline and pipecolic acid
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
US4452790A (en) *	1982-06-23	1984-06-05	E. R. Squibb & Sons, Inc.	Phosphonyl hydroxyacyl amino acid derivatives as antihypertensives
US4616005A (en) *	1982-06-23	1986-10-07	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
US4567166A (en) *	1982-07-14	1986-01-28	E. R. Squibb & Sons, Inc.	Amino and substituted amino phosphinylalkanoyl compounds useful for treating hypertension
EP0187037A3 (en) *	1984-12-21	1988-03-23	Takeda Chemical Industries, Ltd.	Piperidine derivatives, their production and use
CA2021409A1 (en) *	1989-08-21	1991-02-22	Donald S. Karanewsky	Phosphonate substituted amino or imino acids useful as antihypertensives
EP0640594A1 (en)	1993-08-23	1995-03-01	Fujirebio Inc.	Hydantoin derivative as metalloprotease inhibitor
US5435286A (en) *	1994-05-02	1995-07-25	Cummins Engine Company, Inc.	Ball link assembly for vehicle engine drive trains
US7659305B2 (en)	2002-10-31	2010-02-09	Pfizer Inc.	Therapeutic proline derivatives
GB0225379D0 (en) *	2002-10-31	2002-12-11	Pfizer Ltd	Therapeutic proline derivatives
WO2006038119A1 (en) *	2004-10-08	2006-04-13	Warner-Lambert Company Llc	Stereoselective synthesis of n-protected alkoxy prolines
GB0715626D0 (en) *	2007-08-10	2007-09-19	Generics Uk Ltd	Crystalline form of zofenopril calcium
JP5530369B2 (ja) *	2008-02-27	2014-06-25	ジェネリクス・［ユーケー］・リミテッド	新規な結晶形
US8853421B2 (en)	2008-02-27	2014-10-07	Generics [Uk] Limited	Crystalline forms of zofenopril calcium
SI23949A (sl)	2011-12-19	2013-06-28	Silverstone Pharma	Nove kristalne soli zofenoprila, postopek za njihovo dobivanje in njihova uporaba v terapiji

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2340092A2 (fr) *	1976-02-09	1977-09-02	Roussel Uclaf	Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament
AU509899B2 (en) *	1976-02-13	1980-05-29	E.R. Squibb & Sons, Inc.	Proline derivatives and related compounds
US4116962A (en) *	1976-12-03	1978-09-26	E. R. Squibb & Sons, Inc.	Pyrrolidine and piperidine-2-carboxylic acid derivatives
US4113715A (en) *	1977-01-17	1978-09-12	E. R. Squibb & Sons, Inc.	Amino acid derivatives
US4108886A (en) *	1977-03-11	1978-08-22	E. R. Squibb & Sons, Inc.	Thiopropanoylamino acid derivatives
PH15381A (en) *	1978-02-21	1982-12-17	Squibb & Sons Inc	Halogen substituted mercaptoacylamino acids
US4154934A (en) *	1978-08-11	1979-05-15	E. R. Squibb & Sons, Inc.	Mercaptoacylamino derivatives of heterocyclic carboxylic acids

1979
- 1979-07-16 CA CA000331877A patent/CA1144930A/en not_active Expired
- 1979-07-17 NZ NZ191036A patent/NZ191036A/en unknown
- 1979-07-18 GR GR59635A patent/GR72420B/el unknown
- 1979-07-18 IN IN524/DEL/79A patent/IN152712B/en unknown
- 1979-07-18 ZA ZA00793633A patent/ZA793633B/xx unknown
- 1979-07-24 AU AU49190/79A patent/AU530690B2/en not_active Expired
- 1979-07-30 FR FR7919590A patent/FR2435469A1/fr active Granted
- 1979-08-01 PH PH22842A patent/PH15030A/en unknown
- 1979-08-03 IT IT49954/79A patent/IT1117782B/it active Protection Beyond IP Right Term
- 1979-08-07 YU YU1923/79A patent/YU41876B/xx unknown
- 1979-08-07 DE DE2932021A patent/DE2932021C2/de not_active Expired - Lifetime
- 1979-08-08 AT AT0541679A patent/AT379589B/de not_active IP Right Cessation
- 1979-08-09 CS CS795462A patent/CS228118B2/cs unknown
- 1979-08-09 DD DD79214896A patent/DD145749A5/de not_active IP Right Cessation
- 1979-08-10 JP JP10272279A patent/JPS5527199A/ja active Granted
- 1979-08-10 PT PT70049A patent/PT70049A/pt unknown
- 1979-08-10 CH CH737579A patent/CH642064A5/de not_active IP Right Cessation
- 1979-08-10 ES ES483311A patent/ES483311A1/es not_active Expired
- 1979-08-10 LU LU81593A patent/LU81593A1/xx active Protection Beyond IP Right Term
- 1979-08-10 AR AR277678A patent/AR229081A1/es active
- 1979-08-10 GB GB7927867A patent/GB2028327B/en not_active Expired
- 1979-08-10 DK DK335879A patent/DK154553C/da not_active IP Right Cessation
- 1979-08-10 IE IE1544/79A patent/IE48802B1/en active Protection Beyond IP Right Term
- 1979-08-10 FI FI792498A patent/FI69834C/fi not_active IP Right Cessation
- 1979-08-10 KR KR1019790002731A patent/KR830002450B1/ko active
- 1979-08-10 SU SU792800304A patent/SU1066460A3/ru active
- 1979-08-10 BE BE0/196688A patent/BE878191A/fr not_active IP Right Cessation
- 1979-08-10 RO RO98428A patent/RO78870B/ro unknown
- 1979-08-10 NL NL7906120A patent/NL193374C/nl active Protection Beyond IP Right Term
- 1979-08-10 SE SE7906722A patent/SE447477B/sv active Protection Beyond IP Right Term
1988
- 1988-12-21 JP JP63323204A patent/JPH01287069A/ja active Pending
1999
- 1999-06-04 LU LU90403C patent/LU90403I2/fr unknown
- 1999-08-04 NL NL990024C patent/NL990024I1/nl unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH05344844A (ja) *	1992-06-12	1993-12-27	Suzumo Kiko Kk	焼おむすびせんべいの製造方法

Also Published As

Publication number	Publication date
GB2028327A (en)	1980-03-05
NL7906120A (nl)	1980-02-13
CA1144930A (en)	1983-04-19
RO78870A (ro)	1982-07-06
AT379589B (de)	1986-01-27
DE2932021A1 (de)	1980-02-21
ZA793633B (en)	1980-07-30
ATA541679A (de)	1985-06-15
IT7949954A0 (it)	1979-08-03
IE48802B1 (en)	1985-05-15
LU90403I2 (fr)	2000-07-07
DK154553C (da)	1989-04-17
AU530690B2 (en)	1983-07-28
ES483311A1 (es)	1980-04-16
NL990024I2 (nl)	1999-11-01
IT1117782B (it)	1986-02-24
CS228118B2 (en)	1984-05-14
SE7906722L (sv)	1980-02-12
YU192379A (en)	1983-02-28
PT70049A (en)	1979-09-01
NL193374B (nl)	1999-04-01
KR830001269A (ko)	1983-04-29
RO78870B (ro)	1985-01-30
FR2435469A1 (fr)	1980-04-04
FR2435469B1 (ko)	1983-02-11
BE878191A (fr)	1980-02-11
FI792498A (fi)	1980-02-12
YU41876B (en)	1988-02-29
NZ191036A (en)	1984-05-31
CH642064A5 (de)	1984-03-30
DK335879A (da)	1980-02-12
SU1066460A3 (ru)	1984-01-07
JPH01287069A (ja)	1989-11-17
GB2028327B (en)	1982-11-24
AU4919079A (en)	1980-02-14
IN152712B (ko)	1984-03-17
DE2932021C2 (de)	1994-05-19
LU81593A1 (fr)	1979-12-07
DK154553B (da)	1988-11-28
AR229081A1 (es)	1983-06-15
FI69834C (fi)	1986-05-26
NL193374C (nl)	1999-08-03
NL990024I1 (nl)	1999-11-01
IE791544L (en)	1980-02-11
KR830002450B1 (ko)	1983-10-26
GR72420B (ko)	1983-11-03
PH15030A (en)	1982-05-13
FI69834B (fi)	1985-12-31
SE447477B (sv)	1986-11-17
JPS5527199A (en)	1980-02-27
DD145749A5 (de)	1981-01-07

Publication	Publication Date	Title
JPH0134987B2 (ko)	1989-07-21
US4316906A (en)	1982-02-23	Mercaptoacyl derivatives of substituted prolines
US4128653A (en)	1978-12-05	Reduction of blood pressure with carboxyalkylacyl-pipecolic acid derivatives
JPH0212218B2 (ko)	1990-03-19
JPH02191250A (ja)	1990-07-27	４―置換プロリン類
DK157487B (da)	1990-01-15	Analogifremgangsmaade til fremstilling af prolinderivater.
CZ63199A3 (cs)	1999-08-11	Sloučeniny typu substituovaných cyklických aminů jako inhibitory metaloproteáz, způsob jejich přípravy a použití jako léčiv
CZ576590A3 (en)	1995-11-15	Derivatives of amino acids, process of their preparation, their use and medicaments based thereon
DK152495B (da)	1988-03-07	Analogifremgangsmaade til fremstilling af n2-arylsulfonyl-l-argininamider eller farmaceutisk tolerable salte deraf
JPS643870B2 (ko)	1989-01-23
FR2822826A1 (fr)	2002-10-04	Nouveaux derives sulfonyles d'alpha-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
JPS6216944B2 (ko)	1987-04-15
US9469609B2 (en)	2016-10-18	Synthesis of pyrrolidine compounds
US4154937A (en)	1979-05-15	Hydroxycarbamoylalkylacylpipecolic acid compounds
US4296033A (en)	1981-10-20	4-Azido-1-mercaptoacyl proline
EP0468469A2 (en)	1992-01-29	Proline derivatives
WO1997009066A1 (fr)	1997-03-13	INHIBITEUR DE SOLUBILISATION DE LIGAND Fas
JPH0134986B2 (ko)	1989-07-21
US4307110A (en)	1981-12-22	Mercaptoacyl derivatives of 3-substituted proline derivatives
FR2594831A1 (fr)	1987-08-28	Derives de proline, leur procede de preparation, composition pharmaceutique en comportant et procede d'inhibition de l'enzyme transformant l'angiotensine
HU179782B (hu)	1982-12-28	Eljárás merkaptoacil-prolin éter- és tioéter-származékai előállítására
US4308388A (en)	1981-12-29	4-Azido-1-mercaptoacyl pipecolic acid
US4497953A (en)	1985-02-05	Imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids
EP0042639A2 (en)	1981-12-30	Azido, imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids having hypotensive activity
JPH0378378B2 (ko)	1991-12-13

JPH0134987B2 - - Google Patents

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Landscapes

Applications Claiming Priority (2)

Related Child Applications (1)

Publications (2)

Family

ID=26626596

Family Applications (2)

Family Applications After (1)

Country Status (30)

Cited By (1)

Families Citing this family (44)

Family Cites Families (7)

Cited By (1)

Also Published As

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