BE696826A - - Google Patents

Info

Publication number: BE696826A
Authority: BE; Belgium
Prior art keywords: sep; acid; guanidino; formula; group
Prior art date: 1967-04-10

Application number

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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.)

1967-04-10

Filing date

1967-04-10

Publication date

1967-10-10

1967-04-10 Application filed filed Critical

1967-10-10 Publication of BE696826A publication Critical patent/BE696826A/fr

Links

239000000203 mixture Substances 0.000 claims description 47
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
239000002253 acid Substances 0.000 claims description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 37
150000001875 compounds Chemical class 0.000 claims description 37
238000000034 method Methods 0.000 claims description 30
-1 alkyl 4-guanidino butyrate Chemical compound 0.000 claims description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 19
239000003921 oil Substances 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
150000002148 esters Chemical class 0.000 claims description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
150000001408 amides Chemical class 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 11
239000002775 capsule Substances 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 8
239000003377 acid catalyst Substances 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 7
239000007787 solid Substances 0.000 claims description 7
239000000454 talc Substances 0.000 claims description 7
229910052623 talc Inorganic materials 0.000 claims description 7
229910021529 ammonia Inorganic materials 0.000 claims description 6
125000004104 aryloxy group Chemical group 0.000 claims description 6
YHVFECVVGNXFKO-UHFFFAOYSA-N 4-guanidinobutanamide Chemical group NC(=O)CCCNC(N)=N YHVFECVVGNXFKO-UHFFFAOYSA-N 0.000 claims description 5
229920002472 Starch Polymers 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
239000000829 suppository Substances 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
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125000005843 halogen group Chemical group 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
235000019359 magnesium stearate Nutrition 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
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125000001424 substituent group Chemical group 0.000 claims description 4
240000007472 Leucaena leucocephala Species 0.000 claims description 3
235000010643 Leucaena leucocephala Nutrition 0.000 claims description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
239000003995 emulsifying agent Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 3
239000012454 non-polar solvent Substances 0.000 claims description 3
239000010695 polyglycol Substances 0.000 claims description 3
229920000151 polyglycol Polymers 0.000 claims description 3
239000003755 preservative agent Substances 0.000 claims description 3
239000003381 stabilizer Substances 0.000 claims description 3
239000000375 suspending agent Substances 0.000 claims description 3
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 3
229940070710 valerate Drugs 0.000 claims description 3
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 2
108010010803 Gelatin Proteins 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
239000000443 aerosol Substances 0.000 claims description 2
230000001476 alcoholic effect Effects 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
235000015218 chewing gum Nutrition 0.000 claims description 2
150000001860 citric acid derivatives Chemical class 0.000 claims description 2
229940110456 cocoa butter Drugs 0.000 claims description 2
235000019868 cocoa butter Nutrition 0.000 claims description 2
229950001902 dimevamide Drugs 0.000 claims description 2
239000002270 dispersing agent Substances 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
235000003599 food sweetener Nutrition 0.000 claims description 2
239000008273 gelatin Substances 0.000 claims description 2
229920000159 gelatin Polymers 0.000 claims description 2
235000019322 gelatine Nutrition 0.000 claims description 2
235000011852 gelatine desserts Nutrition 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
150000002688 maleic acid derivatives Chemical class 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
235000010755 mineral Nutrition 0.000 claims description 2
150000002823 nitrates Chemical class 0.000 claims description 2
125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims description 2
235000021317 phosphate Nutrition 0.000 claims description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
239000006187 pill Substances 0.000 claims description 2
239000003380 propellant Substances 0.000 claims description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
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235000020357 syrup Nutrition 0.000 claims description 2
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235000012222 talc Nutrition 0.000 claims description 2
239000002562 thickening agent Substances 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
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125000003710 aryl alkyl group Chemical group 0.000 claims 1
239000000872 buffer Substances 0.000 claims 1
239000004202 carbamide Substances 0.000 claims 1
239000003086 colorant Substances 0.000 claims 1
235000014987 copper Nutrition 0.000 claims 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
IJTGLNHUQGIACX-UHFFFAOYSA-N ethyl 6-(diaminomethylideneamino)hexanoate Chemical class CCOC(=O)CCCCCNC(N)=N IJTGLNHUQGIACX-UHFFFAOYSA-N 0.000 claims 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims 1
150000002500 ions Chemical class 0.000 claims 1
239000008101 lactose Substances 0.000 claims 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
150000007524 organic acids Chemical class 0.000 claims 1
238000005507 spraying Methods 0.000 claims 1
238000005303 weighing Methods 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
239000000243 solution Substances 0.000 description 36
235000019441 ethanol Nutrition 0.000 description 19
239000000047 product Substances 0.000 description 14
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
229910000041 hydrogen chloride Inorganic materials 0.000 description 12
230000032050 esterification Effects 0.000 description 10
238000005886 esterification reaction Methods 0.000 description 10
239000000314 lubricant Substances 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
206010012601 diabetes mellitus Diseases 0.000 description 8
239000007789 gas Substances 0.000 description 8
230000002218 hypoglycaemic effect Effects 0.000 description 8
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 8
QHQKFKHTHUDEQS-UHFFFAOYSA-N 4-(diaminomethylideneamino)butanamide;hydrochloride Chemical compound Cl.NC(=O)CCCN=C(N)N QHQKFKHTHUDEQS-UHFFFAOYSA-N 0.000 description 7
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 7
239000008187 granular material Substances 0.000 description 7
230000000694 effects Effects 0.000 description 6
210000004369 blood Anatomy 0.000 description 5
239000008280 blood Substances 0.000 description 5
TUHVEAJXIMEOSA-UHFFFAOYSA-N gamma-guanidinobutyric acid Natural products NC(=[NH2+])NCCCC([O-])=O TUHVEAJXIMEOSA-UHFFFAOYSA-N 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
238000003756 stirring Methods 0.000 description 5
APIBROGXENTUGB-ZUQRMPMESA-M triphenyl-[(e)-3-phenylprop-2-enyl]phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C\C=C\C1=CC=CC=C1 APIBROGXENTUGB-ZUQRMPMESA-M 0.000 description 5
102000004877 Insulin Human genes 0.000 description 4
108090001061 Insulin Proteins 0.000 description 4
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241000283973 Oryctolagus cuniculus Species 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000002347 injection Methods 0.000 description 4
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229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
WUSLRLHRBWDTDJ-UHFFFAOYSA-N methyl 4-(diaminomethylideneamino)butanoate;hydrochloride Chemical compound Cl.COC(=O)CCCN=C(N)N WUSLRLHRBWDTDJ-UHFFFAOYSA-N 0.000 description 1
KVQGGLZHHFGHPU-UHFFFAOYSA-N methyl 4-aminobutanoate Chemical compound COC(=O)CCCN KVQGGLZHHFGHPU-UHFFFAOYSA-N 0.000 description 1
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000005445 natural material Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
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 description 1
239000003495 polar organic solvent Substances 0.000 description 1
235000015277 pork Nutrition 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

BE696826D 1967-04-10 1967-04-10 BE696826A (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
BE696826		1967-04-10

Publications (1)

Publication Number	Publication Date
BE696826A true BE696826A (no)	1967-10-10

Family

ID=3850597

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE696826D BE696826A (no)	1967-04-10	1967-04-10

Country Status (1)

Country	Link
BE (1)	BE696826A (no)

1967
- 1967-04-10 BE BE696826D patent/BE696826A/fr unknown

Publication	Publication Date	Title
EP0033255B1 (fr)	1984-08-29	Nouvelles oximes dérivées de l'érythromycine A, leur préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant
CH643546A5 (fr)	1984-06-15	Procede pour la preparation de derives d'hydantoine.
FR2530625A1 (fr)	1984-01-27	Derives d'indole, procedes pour leur preparation et compositions pharmaceutiques les contenant
BE1015037A6 (fr)	2004-08-03	FORME CRISTALLINE DE LA 2-METHYL-4-(4-METHYL-1-PIPERAZINYL) 10H-THIENO (2,3-b)(1,5)BENZODIAZEPINE.
DE3514696A1 (de)	1986-11-06	N-indolylethyl-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung
EP0015038B1 (fr)	1984-12-19	Composition pharmaceutique comprenant un dérivé de diphénylhydantoine, dérivés mis en oeuvre et leur préparation
CH644348A5 (fr)	1984-07-31	Amino-ethers oxydes, leur procede de preparation et medicament les contenant.
EP0677042B1 (fr)	1998-07-22	Ligands selectifs des recepteurs 5ht1d-5ht1b derives d'indole-piperazine utiles comme medicaments
EP0302980A1 (fr)	1989-02-15	1,4-Dihydropyridines, leur procédé de préparation et leur application comme médicaments
EP0133103B1 (fr)	1987-11-11	Benzyl-phényl-osides, procédé de préparation et utilisation
FR2460287A1 (fr)	1981-01-23	9-aminoalkylfluorenes, leur preparation et leur utilisation therapeutique
EP0576619A1 (fr)	1994-01-05	Compositions therapeutiques a base de derives de 1,2-dithiole-3-thione.
BE696826A (no)	1967-10-10
LU81554A1 (de)	1980-02-14	Alkylthiophenoxyalkylamines
FI93442C (fi)	1995-04-10	Menetelmä uusien kysteiinijohdannaisten valmistamiseksi
LU84860A1 (fr)	1984-03-07	Nouveau derive de la pyrazolo(1,5-a)pyridine,sa preparation et les compositions pharmaceutiques qui le contiennent
EP0236646A1 (fr)	1987-09-16	Nouveaux ortho-anisamides, leur procédé d'obtention et leurs applications thérapeutiques
FR2788275A1 (fr)	2000-07-13	((aminoiminomethyl)amino) alcane carboxamides et leurs applications en therapeutique
CH646146A5 (fr)	1984-11-15	Derive du 1alpha,25-dihydroxy cholecalciferol et son procede de preparation.
CH407147A (fr)	1966-02-15	Procédé de préparation de composés antitumoraux
FR2507180A1 (fr)	1982-12-10	Nouvelles phenylalkylamines, leur preparation et leur application comme medicaments
EP0427605A1 (fr)	1991-05-15	Nouveaux dérivés de la morpholine, leur procédé de préparation et les compositions pharmaceutiques les renfermant
FR2610322A1 (fr)	1988-08-05	Nouveaux derives de la pilocarpine, leur preparation et leur utilisation comme medicaments
MC1806A1 (fr)	1987-12-22	Naphtothiazocinones
FR2489825A1 (fr)	1982-03-12	4-carbamoyloxy-oxazaphosphorines, procede pour leur preparation et compositions pharmaceutiques qui les contiennent