CA1106851A - Derives de l-arginine n.sup.2-substitues et leurs sels d'addition acide pour usage pharmaceutique - Google Patents

Derives de l-arginine n.sup.2-substitues et leurs sels d'addition acide pour usage pharmaceutique

Info

Publication number: CA1106851A
Authority: CA; Canada
Prior art keywords: group; alkyl; substituted; formula; alkoxy
Prior art date: 1975-08-08
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

CA257,283A

Other languages

English (en)

Inventor

Shosuke Okamoto

Ryoji Kikumoto

Yoshikuni Tamao

Kazuo Ohkubo

Tohru Tezuka

Shinji Tonomura

Akiko Hijikata

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.)

Mitsubishi Kasei Corp

Original Assignee

Mitsubishi Kasei Corp

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.)

1975-08-08

Filing date

1976-07-19

Publication date

1981-08-11

1975-08-08 Priority claimed from JP9641775A external-priority patent/JPS5941991B2/ja

1975-09-02 Priority claimed from JP50106139A external-priority patent/JPS5913500B2/ja

1975-09-11 Priority claimed from JP50110242A external-priority patent/JPS5913501B2/ja

1975-10-01 Priority claimed from JP11852575A external-priority patent/JPS5913503B2/ja

1975-10-07 Priority claimed from JP12117375A external-priority patent/JPS5822030B2/ja

1976-07-19 Application filed by Mitsubishi Kasei Corp filed Critical Mitsubishi Kasei Corp

1981-08-11 Application granted granted Critical

1981-08-11 Publication of CA1106851A publication Critical patent/CA1106851A/fr

Status Expired legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims abstract description 115
150000003839 salts Chemical class 0.000 title claims abstract description 107
150000001408 amides Chemical class 0.000 claims abstract description 15
-1 thionyl halide Chemical class 0.000 claims description 153
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 140
238000000034 method Methods 0.000 claims description 76
125000001841 imino group Chemical group [H]N=* 0.000 claims description 47
239000000126 substance Substances 0.000 claims description 46
125000003710 aryl alkyl group Chemical group 0.000 claims description 44
125000003545 alkoxy group Chemical group 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
125000002252 acyl group Chemical group 0.000 claims description 25
150000002431 hydrogen Chemical class 0.000 claims description 25
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 23
125000006239 protecting group Chemical group 0.000 claims description 19
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 16
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 15
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 13
125000001188 haloalkyl group Chemical group 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 12
125000004663 dialkyl amino group Chemical group 0.000 claims description 11
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical group 0.000 claims description 10
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
150000003461 sulfonyl halides Chemical class 0.000 claims description 7
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
229910006080 SO2X Inorganic materials 0.000 claims description 6
238000007327 hydrogenolysis reaction Methods 0.000 claims description 6
229930064664 L-arginine Natural products 0.000 claims description 5
235000014852 L-arginine Nutrition 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 4
ULEBESPCVWBNIF-BYPYZUCNSA-N L-arginine amide Chemical compound NC(=O)[C@@H](N)CCCNC(N)=N ULEBESPCVWBNIF-BYPYZUCNSA-N 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 58
238000004519 manufacturing process Methods 0.000 claims 47
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 27
125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 26
125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 22
125000000753 cycloalkyl group Chemical group 0.000 claims 13
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 12
125000003282 alkyl amino group Chemical group 0.000 claims 10
125000001691 aryl alkyl amino group Chemical group 0.000 claims 10
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 6
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims 6
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 claims 6
125000003342 alkenyl group Chemical group 0.000 claims 6
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 2
102100031083 Uteroglobin Human genes 0.000 claims 1
108090000203 Uteroglobin Proteins 0.000 claims 1
208000007536 Thrombosis Diseases 0.000 abstract description 5
230000005764 inhibitory process Effects 0.000 abstract 1
239000008177 pharmaceutical agent Substances 0.000 abstract 1
230000001629 suppression Effects 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
239000002904 solvent Substances 0.000 description 34
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 31
238000006243 chemical reaction Methods 0.000 description 24
150000002148 esters Chemical class 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 12
239000000047 product Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
230000002829 reductive effect Effects 0.000 description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000015271 coagulation Effects 0.000 description 6
238000005345 coagulation Methods 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
230000002785 anti-thrombosis Effects 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
108010049003 Fibrinogen Proteins 0.000 description 4
102000008946 Fibrinogen Human genes 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
229940012952 fibrinogen Drugs 0.000 description 4
239000000725 suspension Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
108090000190 Thrombin Proteins 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003377 acid catalyst Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
239000003146 anticoagulant agent Substances 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
238000009835 boiling Methods 0.000 description 3
150000001718 carbodiimides Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
229940124280 l-arginine Drugs 0.000 description 3
239000000463 material Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000036647 reaction Effects 0.000 description 3
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
229960004072 thrombin Drugs 0.000 description 3
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 2
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
241001547070 Eriodes Species 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
241001465754 Metazoa Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
230000009089 cytolysis Effects 0.000 description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical class CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000001802 infusion Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
230000000670 limiting effect Effects 0.000 description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
GXXCPULTFYZSJG-UHFFFAOYSA-N 4,6-dimethoxynaphthalene-2-sulfonyl chloride Chemical compound C1=C(S(Cl)(=O)=O)C=C(OC)C2=CC(OC)=CC=C21 GXXCPULTFYZSJG-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
241000219498 Alnus glutinosa Species 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
102000009123 Fibrin Human genes 0.000 description 1
108010073385 Fibrin Proteins 0.000 description 1
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WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
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229920006063 Lamide® Polymers 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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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 1
229930006000 Sucrose Natural products 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000193803 Therea Species 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
241000009298 Trigla lyra Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
MIJRUQYZDSEMBD-UHFFFAOYSA-N acetic acid;morpholine Chemical compound CC(O)=O.C1COCCN1 MIJRUQYZDSEMBD-UHFFFAOYSA-N 0.000 description 1
229940022682 acetone Drugs 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005530 alkylenedioxy group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229960004676 antithrombotic agent Drugs 0.000 description 1
229960003121 arginine Drugs 0.000 description 1
125000002102 aryl alkyloxo group Chemical group 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
125000006309 butyl amino group Chemical group 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
229960004424 carbon dioxide Drugs 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000004040 coloring Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000008021 deposition Effects 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
RPFXMGGIQREZOH-ILKKLZGPSA-N ethyl (2s)-2-amino-5-(diaminomethylideneamino)pentanoate;dihydrochloride Chemical compound Cl.Cl.CCOC(=O)[C@@H](N)CCCN=C(N)N RPFXMGGIQREZOH-ILKKLZGPSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
229950003499 fibrin Drugs 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
CBCIHIVRDWLAME-UHFFFAOYSA-N hexanitrodiphenylamine Chemical class [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O CBCIHIVRDWLAME-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 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
150000003854 isothiazoles Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
230000002101 lytic effect Effects 0.000 description 1
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000004893 oxazines Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
239000012488 sample solution Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
150000004897 thiazines Chemical class 0.000 description 1
230000001732 thrombotic effect Effects 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/24—[b,e]-condensed with two six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Peptides Or Proteins (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA257,283A 1975-08-08 1976-07-19 Derives de l-arginine n.sup.2-substitues et leurs sels d'addition acide pour usage pharmaceutique Expired CA1106851A (fr)

Applications Claiming Priority (10)

Application Number	Priority Date	Filing Date	Title
JP9641775A JPS5941991B2 (ja)	1975-08-08	1975-08-08	Ｎ↑２−置換アルギニンアミド類またはその酸付加塩の製造法
JP96417-1975		1975-08-08
JP50106139A JPS5913500B2 (ja)	1975-09-02	1975-09-02	Ｎ↑２−ナフタレンスルホニルアルギニンアミド類またはその酸付加塩の製造法
JP106139-1975		1975-09-02
JP110242-1975		1975-09-11
JP50110242A JPS5913501B2 (ja)	1975-09-11	1975-09-11	Ｎ↑２−ナフタレンスルホニルアルギニンアミド類またはその酸付加塩の製造法
JP118525-1975		1975-10-01
JP11852575A JPS5913503B2 (ja)	1975-10-01	1975-10-01	Ｎ↑２−ナフタレンスルホニルアルギニンエステルもしくはアミド類またはそれらの酸付加塩の製造法
JP121173-1975		1975-10-07
JP12117375A JPS5822030B2 (ja)	1975-10-07	1975-10-07	Ｎ２− ナフタレンスルホニルアルギニンエステルルイマタハソノサンフカエンノセイゾウホウ

Publications (1)

Publication Number	Publication Date
CA1106851A true CA1106851A (fr)	1981-08-11

Family

ID=27525790

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA257,283A Expired CA1106851A (fr)	1975-08-08	1976-07-19	Derives de l-arginine n.sup.2-substitues et leurs sels d'addition acide pour usage pharmaceutique

Country Status (9)

Country	Link
CA (1)	CA1106851A (fr)
CH (3)	CH632243A5 (fr)
DE (1)	DE2635548C2 (fr)
DK (1)	DK357876A (fr)
FR (1)	FR2320088A1 (fr)
GB (1)	GB1530667A (fr)
NL (1)	NL7608784A (fr)
NO (1)	NO762744L (fr)
SE (1)	SE428014B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9504350D0 (en) *	1995-03-04	1995-04-26	Sod Conseils Rech Applic	Arginine derivatives

1976
- 1976-07-19 CA CA257,283A patent/CA1106851A/fr not_active Expired
- 1976-08-04 CH CH996676A patent/CH632243A5/de not_active IP Right Cessation
- 1976-08-06 NO NO762744A patent/NO762744L/no unknown
- 1976-08-06 GB GB32910/76A patent/GB1530667A/en not_active Expired
- 1976-08-06 NL NL7608784A patent/NL7608784A/xx not_active Application Discontinuation
- 1976-08-06 DE DE2635548A patent/DE2635548C2/de not_active Expired
- 1976-08-06 DK DK357876A patent/DK357876A/da not_active Application Discontinuation
- 1976-08-09 FR FR7624336A patent/FR2320088A1/fr active Granted
- 1976-08-25 SE SE7608791A patent/SE428014B/xx not_active IP Right Cessation
1981
- 1981-06-10 CH CH379881A patent/CH629764A5/de not_active IP Right Cessation
- 1981-06-10 CH CH379781A patent/CH628880A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK357876A (da)	1977-02-09
FR2320088B1 (fr)	1978-12-22
NL7608784A (nl)	1977-02-10
GB1530667A (en)	1978-11-01
DE2635548C2 (de)	1985-05-23
CH629764A5 (en)	1982-05-14
SE428014B (sv)	1983-05-30
SE7608791L (sv)	1977-02-09
NO762744L (fr)	1977-02-09
FR2320088A1 (fr)	1977-03-04
CH632243A5 (en)	1982-09-30
DE2635548A1 (de)	1977-03-03
CH628880A5 (en)	1982-03-31

Legal Events

Date	Code	Title	Description
1998-08-11	MKEX	Expiry

Publication	Publication Date	Title
CA1104569A (fr)	1981-07-07	Traduction non-disponible
EP0288973B1 (fr)	1993-01-13	Dérivés de benzothiazolinone, leur préparation et composition pharmaceutique
US2846437A (en)	1958-08-05	Lower alkyl 4-phenyl-1-(substituted-alkyl) piperidine-4-carboxylates and preparationthereof
GB2054588A (en)	1981-02-18	Amino-ether oxides and pharmaceutical formulations thereof
DK145376B (da)	1982-11-08	Analogifremgangsmaade til fremstilling af n-(1'-benzyl-2'-pyrrolidinylmethyl)-benzamider eller syreadditionssalte,kvaternaere ammoniumsalte eller optisk aktive isomere deraf
US4334067A (en)	1982-06-08	Flavan compounds and acid addition salts thereof
US4264613A (en)	1981-04-28	Piperidylbenzimidazolinone compounds
JPH03218367A (ja)	1991-09-25	ナフチルオキサゾリドン誘導体、その製法及びその合成中間体
EP0386667B1 (fr)	1993-11-18	6-Amino-6-désoxyfumagillols, leur production et leur utilisation
US3395146A (en)	1968-07-30	4-substituted-2-benzhydryl-2-butanol derivatives
CA1106851A (fr)	1981-08-11	Derives de l-arginine n.sup.2-substitues et leurs sels d'addition acide pour usage pharmaceutique
JPS59181273A (ja)	1984-10-15	新規の４′−フラボンカルボン酸、製薬上許容し得るこれら酸の誘導体、その製法及び治療剤としての使用
US4242348A (en)	1980-12-30	Novel basic substituted-alkylidenamino-oxylalkyl-carboxylic-acid esters
US5093332A (en)	1992-03-03	Substituted thieno(2,3-b)(1,4)thiazine-6-sulfonamides as antiglaucoma agents
NO180585B (no)	1997-02-03	Analogifremgangsmåte ved fremstilling av terapeutisk aktive benzoksazinon- og benzotiazinonderivater og mellomprodukter
FI83782C (fi)	1991-08-26	Foerfarande foer framstaellning av farmakologiskt vaerdefulla substituerande isoxazolderivat.
US4071559A (en)	1978-01-31	Pharmaceutically active 2-omega-aminoalkoxydiphenyls
EP0268396B1 (fr)	1990-11-28	4-(Benzoyl)thiophène(ou furanne)-sulfonamide et dérivés pour le traitement topique de l'hypertension intra-oculaire
US2993934A (en)	1961-07-25	Derivatives of pentachlorophenol
US4505923A (en)	1985-03-19	Ethers of hydroxybenzothiazole-2-sulfonamide for the topical treatment of elevated intraocular pressure
NO792590L (no)	1980-02-25	Alfa-aminofenyleddiksyrederivater.
US3420839A (en)	1969-01-07	Aminomethyl pyrazolone derivatives of nicotinamide
NZ201938A (en)	1985-04-30	Anthranilic acid esters,and pharmaceutical compositions containing such
JP2886586B2 (ja)	1999-04-26	新規グアニジノ安息香酸誘導体及びその酸付加塩
US3631035A (en)	1971-12-28	2-vinyl-1 4-dihydroquinazoline derivatives