CA1044142A - Dipeptide anti-inflammatoire - Google Patents

Dipeptide anti-inflammatoire

Info

Publication number: CA1044142A
Authority: CA; Canada
Prior art keywords: composition; dipeptide; active ingredient; liquid; solid form
Prior art date: 1975-07-04
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

CA230,772A

Other languages

English (en)

Other versions

CA230772S (en

Inventor

John N. Mcarthur

Peter D. Dawkins

Mervyn J. H. Smith

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.)

Individual

Original Assignee

Individual

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.)

1975-07-04

Filing date

1975-07-04

Publication date

1978-12-12

1975-07-04 Application filed by Individual filed Critical Individual

1975-07-04 Priority to CA230,772A priority Critical patent/CA1044142A/fr

1978-12-12 Application granted granted Critical

1978-12-12 Publication of CA1044142A publication Critical patent/CA1044142A/fr

Status Expired legal-status Critical Current

Links

108010016626 Dipeptides Proteins 0.000 title claims abstract description 39
230000003110 anti-inflammatory effect Effects 0.000 title description 6
239000000203 mixture Substances 0.000 claims abstract description 40
150000003839 salts Chemical class 0.000 claims abstract description 25
239000007788 liquid Substances 0.000 claims abstract description 20
239000004480 active ingredient Substances 0.000 claims abstract description 14
239000007787 solid Substances 0.000 claims abstract description 11
239000002702 enteric coating Substances 0.000 claims abstract description 9
238000009505 enteric coating Methods 0.000 claims abstract description 9
238000002347 injection Methods 0.000 claims abstract description 8
239000007924 injection Substances 0.000 claims abstract description 8
238000011282 treatment Methods 0.000 claims abstract description 8
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
125000001041 indolyl group Chemical group 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
206010061218 Inflammation Diseases 0.000 claims description 12
230000004054 inflammatory process Effects 0.000 claims description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
229920001800 Shellac Polymers 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
229940081734 cellulose acetate phthalate Drugs 0.000 claims description 4
238000004090 dissolution Methods 0.000 claims description 4
239000004208 shellac Substances 0.000 claims description 4
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 claims description 4
229940113147 shellac Drugs 0.000 claims description 4
235000013874 shellac Nutrition 0.000 claims description 4
-1 D-tryptophanyl D-tryptophan Chemical compound 0.000 claims description 3
NQIHMZLGCZNZBN-PXNSSMCTSA-N Trp-Trp Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)N)C(O)=O)=CNC2=C1 NQIHMZLGCZNZBN-PXNSSMCTSA-N 0.000 claims description 3
JMCOUWKXLXDERB-SJLPKXTDSA-N (2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@@H](N)C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)C1=CC=CC=C1 JMCOUWKXLXDERB-SJLPKXTDSA-N 0.000 claims description 2
GKZIWHRNKRBEOH-HZPDHXFCSA-N (2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](N)C(=O)N[C@H](CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 GKZIWHRNKRBEOH-HZPDHXFCSA-N 0.000 claims description 2
IMMPMHKLUUZKAZ-SJLPKXTDSA-N (2r)-2-[[(2r)-2-azaniumyl-3-(1h-indol-3-yl)propanoyl]amino]-3-phenylpropanoate Chemical compound C([C@@H](NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)N)C(O)=O)C1=CC=CC=C1 IMMPMHKLUUZKAZ-SJLPKXTDSA-N 0.000 claims description 2
229930182827 D-tryptophan Natural products 0.000 claims 1
241000124008 Mammalia Species 0.000 abstract description 4
239000000243 solution Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 6
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 5
150000001413 amino acids Chemical class 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
238000000034 method Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
229960004799 tryptophan Drugs 0.000 description 4
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 3
239000002260 anti-inflammatory agent Substances 0.000 description 3
229940121363 anti-inflammatory agent Drugs 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000000994 depressogenic effect Effects 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
229920000609 methyl cellulose Polymers 0.000 description 3
229960002900 methylcellulose Drugs 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012530 fluid Substances 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
239000006187 pill Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 2
210000002784 stomach Anatomy 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
NQIHMZLGCZNZBN-YLJYHZDGSA-N (2r)-2-[[(2r)-2-amino-3-(1h-indol-3-yl)propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(C[C@@H](NC(=O)[C@@H](CC=3C4=CC=CC=C4NC=3)N)C(O)=O)=CNC2=C1 NQIHMZLGCZNZBN-YLJYHZDGSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
102000009027 Albumins Human genes 0.000 description 1
108010088751 Albumins Proteins 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
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
102000035195 Peptidases Human genes 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
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
240000006474 Theobroma bicolor Species 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000008272 agar Substances 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000002662 enteric coated tablet Substances 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
229960004667 ethyl cellulose Drugs 0.000 description 1
239000001761 ethyl methyl cellulose Substances 0.000 description 1
235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
239000003925 fat Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 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
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
235000019833 protease Nutrition 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
230000008961 swelling Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
239000002562 thickening agent Substances 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
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1

Landscapes

Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA230,772A 1975-07-04 1975-07-04 Dipeptide anti-inflammatoire Expired CA1044142A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA230,772A CA1044142A (fr)	1975-07-04	1975-07-04	Dipeptide anti-inflammatoire

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA230,772A CA1044142A (fr)	1975-07-04	1975-07-04	Dipeptide anti-inflammatoire

Publications (1)

Publication Number	Publication Date
CA1044142A true CA1044142A (fr)	1978-12-12

Family

ID=4103533

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA230,772A Expired CA1044142A (fr)	1975-07-04	1975-07-04	Dipeptide anti-inflammatoire

Country Status (1)

Country	Link
CA (1)	CA1044142A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4757151A (en) *	1985-11-14	1988-07-12	Warner-Lambert Company	2-substituted-[2-substituted-amino]-N-arylalkyl-3-[indol-3-yl]

1975
- 1975-07-04 CA CA230,772A patent/CA1044142A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4757151A (en) *	1985-11-14	1988-07-12	Warner-Lambert Company	2-substituted-[2-substituted-amino]-N-arylalkyl-3-[indol-3-yl]

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CA1044142A - Dipeptide anti-inflammatoire - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4103533

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

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