CH628811A5 - Injection solutions - Google Patents

Injection solutions Download PDF

Info

Publication number: CH628811A5
Authority: CH; Switzerland
Prior art keywords: injection solutions; solutions according; micelle; acid; contain
Prior art date: 1976-07-12

Application number

CH699477A

Other languages

German (de)

English (en)

Inventor

Hans Dr Steffen

Dieter Dr Schmidt

Original Assignee

Hoffmann La Roche

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.)

1976-07-12

Filing date

1977-06-07

Publication date

1982-03-31

1977-06-07 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1977-06-29 Priority to IT25194/77A priority Critical patent/IT1202370B/it

1977-07-05 Priority to NZ184564A priority patent/NZ184564A/xx

1977-07-05 Priority to IL52458A priority patent/IL52458A/xx

1977-07-06 Priority to IE1403/77A priority patent/IE46037B1/en

1977-07-06 Priority to DE19772730570 priority patent/DE2730570A1/de

1977-07-07 Priority to AU26846/77A priority patent/AU517249B2/en

1977-07-07 Priority to FR7720957A priority patent/FR2358161A1/fr

1977-07-08 Priority to CA282,347A priority patent/CA1082596A/fr

1977-07-08 Priority to US05/813,913 priority patent/US4158707A/en

1977-07-08 Priority to LU77708A priority patent/LU77708A1/xx

1977-07-08 Priority to NLAANVRAGE7707641,A priority patent/NL189072C/xx

1977-07-08 Priority to JP52081110A priority patent/JPS6051448B2/ja

1977-07-11 Priority to GB29006/77A priority patent/GB1587076A/en

1977-07-11 Priority to SE7708059A priority patent/SE448516B/xx

1977-07-11 Priority to DK314777A priority patent/DK149483C/da

1977-07-12 Priority to PH19986A priority patent/PH16333A/en

1978-12-28 Priority to FR7836690A priority patent/FR2423219A1/fr

1982-03-31 Publication of CH628811A5 publication Critical patent/CH628811A5/de

1984-03-22 Priority to HK265/84A priority patent/HK26584A/xx

1985-12-30 Priority to MY263/85A priority patent/MY8500263A/xx

1997-03-12 Priority to LU90037C priority patent/LU90037I2/fr

Links

239000000243 solution Substances 0.000 title claims abstract description 59
239000007924 injection Substances 0.000 title claims abstract description 46
238000002347 injection Methods 0.000 title claims abstract description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
239000003814 drug Substances 0.000 claims abstract description 16
239000000126 substance Substances 0.000 claims abstract description 13
HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical class C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims abstract description 12
239000000654 additive Substances 0.000 claims abstract description 12
229940079593 drug Drugs 0.000 claims abstract description 5
239000000693 micelle Substances 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
239000008363 phosphate buffer Substances 0.000 claims description 8
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
229920002685 Polyoxyl 35CastorOil Polymers 0.000 claims description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
239000000872 buffer Substances 0.000 claims description 6
KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
150000002632 lipids Chemical class 0.000 claims description 6
QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 claims description 6
229920001983 poloxamer Polymers 0.000 claims description 6
239000008389 polyethoxylated castor oil Substances 0.000 claims description 6
229920000136 polysorbate Polymers 0.000 claims description 6
150000003431 steroids Chemical group 0.000 claims description 6
150000008105 phosphatidylcholines Chemical class 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
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 claims description 4
108010007979 Glycocholic Acid Proteins 0.000 claims description 4
206010018910 Haemolysis Diseases 0.000 claims description 4
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 claims description 4
RFDAIACWWDREDC-UHFFFAOYSA-N Na salt-Glycocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCC(O)=O)C)C1(C)C(O)C2 RFDAIACWWDREDC-UHFFFAOYSA-N 0.000 claims description 4
150000001413 amino acids Chemical class 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
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 claims description 4
ZGSPNIOCEDOHGS-UHFFFAOYSA-L disodium [3-[2,3-di(octadeca-9,12-dienoyloxy)propoxy-oxidophosphoryl]oxy-2-hydroxypropyl] 2,3-di(octadeca-9,12-dienoyloxy)propyl phosphate Chemical compound [Na+].[Na+].CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC(O)COP([O-])(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC ZGSPNIOCEDOHGS-UHFFFAOYSA-L 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
239000008103 glucose Substances 0.000 claims description 4
RFDAIACWWDREDC-FRVQLJSFSA-N glycocholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 RFDAIACWWDREDC-FRVQLJSFSA-N 0.000 claims description 4
229940099347 glycocholic acid Drugs 0.000 claims description 4
230000008588 hemolysis Effects 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
125000000468 ketone group Chemical group 0.000 claims description 4
238000007911 parenteral administration Methods 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims description 3
RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 claims description 3
GHCZTIFQWKKGSB-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;phosphoric acid Chemical compound OP(O)(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O GHCZTIFQWKKGSB-UHFFFAOYSA-N 0.000 claims description 3
239000004380 Cholic acid Substances 0.000 claims description 3
JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 3
239000004471 Glycine Substances 0.000 claims description 3
108010015031 Glycochenodeoxycholic Acid Proteins 0.000 claims description 3
108010035713 Glycodeoxycholic Acid Proteins 0.000 claims description 3
WVULKSPCQVQLCU-UHFFFAOYSA-N Glycodeoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCC(O)=O)C)C1(C)C(O)C2 WVULKSPCQVQLCU-UHFFFAOYSA-N 0.000 claims description 3
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
BHTRKEVKTKCXOH-UHFFFAOYSA-N Taurochenodesoxycholsaeure Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCCS(O)(=O)=O)C)C1(C)CC2 BHTRKEVKTKCXOH-UHFFFAOYSA-N 0.000 claims description 3
WBWWGRHZICKQGZ-UHFFFAOYSA-N Taurocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCCS(O)(=O)=O)C)C1(C)C(O)C2 WBWWGRHZICKQGZ-UHFFFAOYSA-N 0.000 claims description 3
239000007983 Tris buffer Substances 0.000 claims description 3
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 3
RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 claims description 3
229960001091 chenodeoxycholic acid Drugs 0.000 claims description 3
BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims description 3
235000019416 cholic acid Nutrition 0.000 claims description 3
229960002471 cholic acid Drugs 0.000 claims description 3
239000007979 citrate buffer Substances 0.000 claims description 3
KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims description 3
229960003964 deoxycholic acid Drugs 0.000 claims description 3
GHCZAUBVMUEKKP-GYPHWSFCSA-N glycochenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)CC1 GHCZAUBVMUEKKP-GYPHWSFCSA-N 0.000 claims description 3
WVULKSPCQVQLCU-BUXLTGKBSA-N glycodeoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 WVULKSPCQVQLCU-BUXLTGKBSA-N 0.000 claims description 3
150000003905 phosphatidylinositols Chemical class 0.000 claims description 3
239000011780 sodium chloride Substances 0.000 claims description 3
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 3
235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 3
235000010262 sodium metabisulphite Nutrition 0.000 claims description 3
159000000000 sodium salts Chemical class 0.000 claims description 3
BHTRKEVKTKCXOH-AYSJQVDDSA-N taurochenodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)C1C2C2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)CC1 BHTRKEVKTKCXOH-AYSJQVDDSA-N 0.000 claims description 3
WBWWGRHZICKQGZ-GIHLXUJPSA-N taurocholic acid Chemical compound C([C@@H]1C[C@H]2O)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@H](O)C1 WBWWGRHZICKQGZ-GIHLXUJPSA-N 0.000 claims description 3
AWDRATDZQPNJFN-VAYUFCLWSA-N taurodeoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 AWDRATDZQPNJFN-VAYUFCLWSA-N 0.000 claims description 3
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
GHCZAUBVMUEKKP-UHFFFAOYSA-N ursodeoxycholic acid glycine-conjugate Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCC(O)=O)C)C1(C)CC2 GHCZAUBVMUEKKP-UHFFFAOYSA-N 0.000 claims description 3
206010002199 Anaphylactic shock Diseases 0.000 claims description 2
206010020751 Hypersensitivity Diseases 0.000 claims description 2
208000003455 anaphylaxis Diseases 0.000 claims description 2
239000003613 bile acid Substances 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
239000000084 colloidal system Substances 0.000 claims description 2
RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 claims description 2
230000002949 hemolytic effect Effects 0.000 claims description 2
230000002101 lytic effect Effects 0.000 claims description 2
150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 2
150000008106 phosphatidylserines Chemical class 0.000 claims description 2
229920001223 polyethylene glycol Polymers 0.000 claims description 2
239000002510 pyrogen Substances 0.000 claims description 2
230000007928 solubilization Effects 0.000 claims description 2
238000005063 solubilization Methods 0.000 claims description 2
239000003981 vehicle Substances 0.000 claims description 2
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 abstract 1
229940067606 lecithin Drugs 0.000 abstract 1
235000010445 lecithin Nutrition 0.000 abstract 1
239000000787 lecithin Substances 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000008344 egg yolk phospholipid Substances 0.000 description 10
238000000034 method Methods 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
229960003529 diazepam Drugs 0.000 description 8
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
OABYVIYXWMZFFJ-ZUHYDKSRSA-M sodium glycocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 OABYVIYXWMZFFJ-ZUHYDKSRSA-M 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
-1 alkali metal salts Chemical class 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000011782 vitamin Substances 0.000 description 3
229940088594 vitamin Drugs 0.000 description 3
235000013343 vitamin Nutrition 0.000 description 3
229930003231 vitamin Natural products 0.000 description 3
150000003722 vitamin derivatives Chemical class 0.000 description 3
PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
229910006069 SO3H Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
235000010378 sodium ascorbate Nutrition 0.000 description 2
PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 2
229960005055 sodium ascorbate Drugs 0.000 description 2
PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 2
239000008347 soybean phospholipid Substances 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
XBWAZCLHZCFCGK-UHFFFAOYSA-N 7-chloro-1-methyl-5-phenyl-3,4-dihydro-2h-1,4-benzodiazepin-1-ium;chloride Chemical compound [Cl-].C12=CC(Cl)=CC=C2[NH+](C)CCN=C1C1=CC=CC=C1 XBWAZCLHZCFCGK-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
VMIYHDSEFNYJSL-UHFFFAOYSA-N Bromazepam Chemical compound C12=CC(Br)=CC=C2NC(=O)CN=C1C1=CC=CC=N1 VMIYHDSEFNYJSL-UHFFFAOYSA-N 0.000 description 1
ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
ABSPRNADVQNDOU-UHFFFAOYSA-N Menaquinone 1 Natural products C1=CC=C2C(=O)C(CC=C(C)C)=C(C)C(=O)C2=C1 ABSPRNADVQNDOU-UHFFFAOYSA-N 0.000 description 1
PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000004347 all-trans-retinol derivatives Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000002924 anti-infective effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
229960005475 antiinfective agent Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
150000001557 benzodiazepines Chemical class 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
229960002729 bromazepam Drugs 0.000 description 1
DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 description 1
229960003120 clonazepam Drugs 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
CITHEXJVPOWHKC-UHFFFAOYSA-N dimyristoyl phosphatidylcholine Chemical compound CCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UHFFFAOYSA-N 0.000 description 1
229960003724 dimyristoylphosphatidylcholine Drugs 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
229960002200 flunitrazepam Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
229960002225 medazepam Drugs 0.000 description 1
KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 description 1
229960001454 nitrazepam Drugs 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000008055 phosphate buffer solution Substances 0.000 description 1
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
235000019175 phylloquinone Nutrition 0.000 description 1
239000011772 phylloquinone Substances 0.000 description 1
MBWXNTAXLNYFJB-NKFFZRIASA-N phylloquinone Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=C(C)C(=O)C2=C1 MBWXNTAXLNYFJB-NKFFZRIASA-N 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229960001898 phytomenadione Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
JAJWGJBVLPIOOH-IZYKLYLVSA-M sodium taurocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 JAJWGJBVLPIOOH-IZYKLYLVSA-M 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
150000003721 vitamin K derivatives Chemical class 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Dispersion Chemistry (AREA)
Biophysics (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH699477A 1976-07-12 1977-06-07 Injection solutions CH628811A5 (en)

Priority Applications (20)

Application Number	Priority Date	Filing Date	Title
IT25194/77A IT1202370B (it)	1976-07-12	1977-06-29	Soluzioni inietabili in cui l'atti vita' emolitica degli agenti di formazione di micelle naturali e' evitata mediante l'aggiunta di lipoidi e relativi prodotti
NZ184564A NZ184564A (en)	1976-07-12	1977-07-05	Injection solution having an aqueous basis and comprising an insoluble pharmacon
IL52458A IL52458A (en)	1976-07-12	1977-07-05	Injectable solutions containing cholanic acid derivatives
IE1403/77A IE46037B1 (en)	1976-07-12	1977-07-06	Injection solutions containing micelle-forming agents
DE19772730570 DE2730570A1 (de)	1976-07-12	1977-07-06	Injektionsloesungen
AU26846/77A AU517249B2 (en)	1976-07-12	1977-07-07	Injectable solution
FR7720957A FR2358161A1 (fr)	1976-07-12	1977-07-07	Solutions injectables a base aqueuse
LU77708A LU77708A1 (fr)	1976-07-12	1977-07-08
US05/813,913 US4158707A (en)	1976-07-12	1977-07-08	Parenteral preparations
CA282,347A CA1082596A (fr)	1976-07-12	1977-07-08	Solutions injectables
NLAANVRAGE7707641,A NL189072C (nl)	1976-07-12	1977-07-08	Werkwijze voor het bereiden van injectieoplossingen.
JP52081110A JPS6051448B2 (ja)	1976-07-12	1977-07-08	注射溶液
DK314777A DK149483C (da)	1976-07-12	1977-07-11	Fremgangsmaade til fremstilling af vandbaserede injektionsoploesninger indeholdende galdesyrederivater, phosphatider og benzodiazepin
SE7708059A SE448516B (sv)	1976-07-12	1977-07-11	Forfarande for framstellning av injektionslosningar pa vattenbasis, innehallande en bensodiazepin som aktiv substans
GB29006/77A GB1587076A (en)	1976-07-12	1977-07-11	Injection solutions containing micelle-forming agents
PH19986A PH16333A (en)	1976-07-12	1977-07-12	Injectable solutions
FR7836690A FR2423219A1 (fr)	1976-07-12	1978-12-28	Solutions injectables a base aqueuse contenant au moins un derive de vitamine k
HK265/84A HK26584A (en)	1976-07-12	1984-03-22	Injection solutions containing micelle-forming agents
MY263/85A MY8500263A (en)	1976-07-12	1985-12-30	Injection solutions containing micelle-forming agents
LU90037C LU90037I2 (fr)	1976-07-12	1997-03-12	Konakion et ses dérivés pharmaceutiquement acceptables

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AT511176A AT352881B (de)	1976-07-12	1976-07-12	Verfahren zur herstellung von injektions- loesungen

Publications (1)

Publication Number	Publication Date
CH628811A5 true CH628811A5 (en)	1982-03-31

Family

ID=3572052

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH699477A CH628811A5 (en)	1976-07-12	1977-06-07	Injection solutions

Country Status (4)

Country	Link
AT (1)	AT352881B (fr)
BE (1)	BE856675A (fr)
CH (1)	CH628811A5 (fr)
ZA (1)	ZA774044B (fr)

1976
- 1976-07-12 AT AT511176A patent/AT352881B/de active
1977
- 1977-06-07 CH CH699477A patent/CH628811A5/de not_active IP Right Cessation
- 1977-07-05 ZA ZA00774044A patent/ZA774044B/xx unknown
- 1977-07-11 BE BE179230A patent/BE856675A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE856675A (fr)	1978-01-11
AT352881B (de)	1979-10-10
ZA774044B (en)	1978-05-30
ATA511176A (de)	1979-03-15

Legal Events

Date	Code	Title	Description
1990-02-15	PUE	Assignment	Owner name: F. HOFFMANN-LA ROCHE AG
1996-03-15	SPCF	Supplementary protection certificate filed	Free format text: IKS 48112, 870213
1996-06-14	SPCF	Supplementary protection certificate filed	Free format text: IKS 48112/870213, 951102
1996-07-31	SPCR	Supplementary protection certificate rejected	Free format text: IKS 48112/870213, 951102
1997-06-30	PL	Patent ceased

Publication	Publication Date	Title
DE2730570C2 (fr)	1989-01-19
EP0011745B1 (fr)	1981-12-30	Composition colloidale aqueuse pour pharmacie et sa préparation
DE69509279T2 (de)	1999-11-25	Wässrige konzentrierte Lösungen enthaltend Argatroban
DE69924740T2 (de)	2005-09-01	Klare wässrige lösungen enthaltend gallensäuren
DE2914788C2 (fr)	1990-06-21
EP0280887B1 (fr)	1992-01-08	Solutions de micelles mixtes contenant des agents antiinflammatoires non-stéroidiques
DE69627651T2 (de)	2003-10-16	Formulierungen und zusammensetzungen von in wasser schwer löslichen camptothecinderivaten
DD201973A5 (de)	1983-08-24	Verfahren zur herstellung von liposomalen arzneimitteln
DD241422A5 (de)	1986-12-10	Aerosolzubereitung mit fluorchlorkohlenwasserstoffen als treibmittel
DE3883206T2 (de)	1994-02-03	Arzneistoff enthaltende fettemulsion des typs "kurz vor gebrauch hergestellt" sowie verfahren zur herstellung einer arzneihaltigen fettemulsion.
DE2914789C2 (fr)	1991-05-29
DE10148065A1 (de)	2003-04-17	(Ester)-Lysolecithine in Liposomen
DE3782480T2 (de)	1993-04-08	Gefriergetrocknete arzneimittel mit phenylchinolincarbonsaeuren.
DE68903736T2 (de)	1993-04-08	Stabilisierte 2-phenyl-1,2-benzisoselenazol-3(2h)-on enthaltende, parenteral anzuwendende loesung und verfahren zu deren herstellung.
CH628811A5 (en)	1982-03-31	Injection solutions
AT356278B (de)	1980-04-25	Verfahren zur herstellung von injektions- loesungen
DE68906513T2 (de)	1993-09-09	Topisch anzuwendende diclofenac enthaltende arzneizubereitungen.
WO1997000671A2 (fr)	1997-01-09	Composition utilisee pour la production de systemes finement disperses, et son procede de preparation
DE4122744A1 (de)	1992-02-13	Wasserhaltiges liposomensystem
DE3042975A1 (de)	1982-09-09	Mikrodispersion mit einem wirkstoff und/oder einem reagens in salzform als disperser phase
DE3509741A1 (de)	1985-09-26	Orale dosierungsform von etoposid
EP0684840B1 (fr)	2000-08-23	Procede de fabrication de solutions aqueuses colloidales de matieres actives difficilement solubles, et lipide utilise pour ce procede
EP0471309A1 (fr)	1992-02-19	Utilisation de micelles mixtes
DE102021212692A1 (de)	2023-05-11	Selbstemulgierende öl-in wasser-mikro- oder nanoemulsion so-wie emulgierende zusammensetzung
EP0240874B1 (fr)	1990-09-12	Préparation de l'hymécromone à résorption élevée et son procédé de préparation