CA1072011A - Solutions stables de tetracycline dans un solvant de 2-pyrrolidone aqueux - Google Patents

Solutions stables de tetracycline dans un solvant de 2-pyrrolidone aqueux

Info

Publication number: CA1072011A
Authority: CA; Canada
Prior art keywords: tetracycline; pyrrolidone; weight; magnesium; aqueous
Prior art date: 1976-12-20
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

CA268,214A

Other languages

English (en)

Inventor

William W. Armstrong

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.)

Pfizer Corp SRL

Original Assignee

Pfizer Corp SRL

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.)

1976-12-20

Filing date

1976-12-20

Publication date

1980-02-19

1976-12-20 Application filed by Pfizer Corp SRL filed Critical Pfizer Corp SRL

1976-12-20 Priority to CA268,214A priority Critical patent/CA1072011A/fr

1980-02-19 Application granted granted Critical

1980-02-19 Publication of CA1072011A publication Critical patent/CA1072011A/fr

Status Expired legal-status Critical Current

Links

HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 title claims abstract description 33
239000004098 Tetracycline Substances 0.000 title claims abstract description 25
229960002180 tetracycline Drugs 0.000 title claims abstract description 25
229930101283 tetracycline Natural products 0.000 title claims abstract description 25
235000019364 tetracycline Nutrition 0.000 title claims abstract description 24
150000003522 tetracyclines Chemical class 0.000 title claims abstract description 23
239000000203 mixture Substances 0.000 claims description 13
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 10
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 10
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 7
239000000395 magnesium oxide Substances 0.000 claims description 7
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 7
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 7
150000002681 magnesium compounds Chemical class 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 4
229940072172 tetracycline antibiotic Drugs 0.000 claims description 2
239000007788 liquid Substances 0.000 claims 1
239000007864 aqueous solution Substances 0.000 abstract description 3
238000007911 parenteral administration Methods 0.000 abstract description 2
230000000699 topical effect Effects 0.000 abstract description 2
239000006184 cosolvent Substances 0.000 abstract 1
238000011200 topical administration Methods 0.000 abstract 1
239000000243 solution Substances 0.000 description 23
150000002500 ions Chemical class 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 7
229960004989 tetracycline hydrochloride Drugs 0.000 description 7
230000000694 effects Effects 0.000 description 6
238000000034 method Methods 0.000 description 6
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
-1 tetracycline calcium complexes Chemical class 0.000 description 3
NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
ADXMPQWGTCFPGL-UHFFFAOYSA-L [Mg+2].O=C.[O-]S[O-] Chemical compound [Mg+2].O=C.[O-]S[O-] ADXMPQWGTCFPGL-UHFFFAOYSA-L 0.000 description 2
HRKQOINLCJTGBK-UHFFFAOYSA-L dioxidosulfate(2-) Chemical compound [O-]S[O-] HRKQOINLCJTGBK-UHFFFAOYSA-L 0.000 description 2
229940017705 formaldehyde sulfoxylate Drugs 0.000 description 2
239000012458 free base Substances 0.000 description 2
SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
LFRHMTZYADABJZ-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)butan-2-amine;hydron;chloride Chemical compound Cl.CCC(N)CC1=CC=C2OCOC2=C1 LFRHMTZYADABJZ-UHFFFAOYSA-N 0.000 description 1
CGLIJZPVEPWKNU-UHFFFAOYSA-N 3,4-dichlorothiolane Chemical compound ClC1CSCC1Cl CGLIJZPVEPWKNU-UHFFFAOYSA-N 0.000 description 1
NLJVXZFCYKWXLH-DXTIXLATSA-N 3-[(3r,6s,9s,12s,15s,17s,20s,22r,25s,28s)-20-(2-amino-2-oxoethyl)-9-(3-aminopropyl)-3,22,25-tribenzyl-15-[(4-hydroxyphenyl)methyl]-6-(2-methylpropyl)-2,5,8,11,14,18,21,24,27-nonaoxo-12-propan-2-yl-1,4,7,10,13,16,19,23,26-nonazabicyclo[26.3.0]hentriacontan Chemical compound C([C@H]1C(=O)N[C@H](C(=O)N[C@@H](CCCN)C(=O)N[C@H](C(N[C@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)N1)=O)CC(C)C)C(C)C)C1=CC=C(O)C=C1 NLJVXZFCYKWXLH-DXTIXLATSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 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
RZCHTMXTKQHYDT-UHFFFAOYSA-N N-Lactoyl ethanolamine Chemical compound CC(O)C(=O)NCCO RZCHTMXTKQHYDT-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
108010021006 Tyrothricin Proteins 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
RKLXDNHNLPUQRB-TVJUEJKUSA-N chembl564271 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]2C(C)SC[C@H](N[C@@H](CC(N)=O)C(=O)NC(=O)[C@@H](NC2=O)CSC1C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)NC(=C)C(=O)N[C@@H](CCCCN)C(O)=O)NC(=O)[C@H]1NC(=O)C(=C\C)/NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2NC(=O)CNC(=O)[C@@H]3CCCN3C(=O)[C@@H](NC(=O)[C@H]3N[C@@H](CC(C)C)C(=O)NC(=O)C(=C)NC(=O)CC[C@H](NC(=O)[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CC=4C5=CC=CC=C5NC=4)CSC3)C(O)=O)C(C)SC2)C(C)C)C(C)SC1)C1=CC=CC=C1 RKLXDNHNLPUQRB-TVJUEJKUSA-N 0.000 description 1
229960005091 chloramphenicol Drugs 0.000 description 1
WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000003814 drug Substances 0.000 description 1
ISXSFOPKZQZDAO-UHFFFAOYSA-N formaldehyde;sodium Chemical compound [Na].O=C ISXSFOPKZQZDAO-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical compound CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
239000011654 magnesium acetate Substances 0.000 description 1
235000011285 magnesium acetate Nutrition 0.000 description 1
229940069446 magnesium acetate Drugs 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
235000011147 magnesium chloride Nutrition 0.000 description 1
229910001425 magnesium ion Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical group C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
108010082567 subtilin Proteins 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229960003281 tyrothricin Drugs 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicinal Preparation (AREA)

CA268,214A 1976-12-20 1976-12-20 Solutions stables de tetracycline dans un solvant de 2-pyrrolidone aqueux Expired CA1072011A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA268,214A CA1072011A (fr)	1976-12-20	1976-12-20	Solutions stables de tetracycline dans un solvant de 2-pyrrolidone aqueux

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA268,214A CA1072011A (fr)	1976-12-20	1976-12-20	Solutions stables de tetracycline dans un solvant de 2-pyrrolidone aqueux

Publications (1)

Publication Number	Publication Date
CA1072011A true CA1072011A (fr)	1980-02-19

Family

ID=4107533

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA268,214A Expired CA1072011A (fr)	1976-12-20	1976-12-20	Solutions stables de tetracycline dans un solvant de 2-pyrrolidone aqueux

Country Status (1)

Country	Link
CA (1)	CA1072011A (fr)

1976
- 1976-12-20 CA CA268,214A patent/CA1072011A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-02-19	MKEX	Expiry

Publication	Publication Date	Title
US4081528A (en)	1978-03-28	Tetracycline compositions
CA1100875A (fr)	1981-05-12	Composes de tetracycline antibiotique
KR0123932B1 (ko)	1997-11-24	소염진통외용첩부제
KR100402570B1 (ko)	2003-12-18	주사용퀴놀론제제
KR840005448A (ko)	1984-11-12	티에노〔3, 2-c〕 피리딘 유도체의 제조방법
US4081527A (en)	1978-03-28	Chlortetracycline compositions
KR890006540A (ko)	1989-06-14	I-데속시노지리마이신 및 i- 데속시만노노지리마이신의 n-치환유도체, 이들의 제조방법 및 의약제로서의 용도
CA1135188A (fr)	1982-11-09	Compositions a base d'oxytetracycline
AU707366B2 (en)	1999-07-08	Long-acting oxytetracycline composition
CA1072011A (fr)	1980-02-19	Solutions stables de tetracycline dans un solvant de 2-pyrrolidone aqueux
CA2256391A1 (fr)	1997-12-11	Derives de peptidyl-arginine aldehyde anticoagulants
CA1072447A (fr)	1980-02-26	Solutions aqueuses, stables de chlortetracycline dans le 2-pyrrolidone
KR930002322A (ko)	1993-02-22	피라졸 유도체
GB9101986D0 (en)	1991-03-13	Pharmaceutical compositions
US4374826A (en)	1983-02-22	Sulfonamide compositions
GB1592053A (en)	1981-07-01	Oxytetracycline compositions
US3873601A (en)	1975-03-25	Anesthetic compounds
EP0021847A2 (fr)	1981-01-07	Compositions injectables de sulfonamide à effet prolongé
FI72651C (fi)	1987-07-10	Foerfarande foer framstaellning av en laongtidsverkande injektionsloesning av sulfametazin.
KR870001153A (ko)	1987-03-11	디페녹시에틸아민 유도체가 함유된 약제조성물 및 그의 생산방법
US3968237A (en)	1976-07-06	Local anaesthetic
US4393054A (en)	1983-07-12	Method of treating cardiac arrhythmia
CA2194576C (fr)	2006-09-12	Compositions a base d'oxytretracycline a action prolongee
US3702865A (en)	1972-11-14	Ethyl 2-methyl-2-n-propylamino-propyl succinate
HU176305B (hu)	1981-01-28	Eljárás stabil tetraciklin-készítmények előállítására