DD140420B5 - Verfahren zur Herstellung detoxifizierter Zubereitungen von Cytostatika - Google Patents
Verfahren zur Herstellung detoxifizierter Zubereitungen von Cytostatika Download PDFInfo
- Publication number
- DD140420B5 DD140420B5 DD20969178A DD20969178A DD140420B5 DD 140420 B5 DD140420 B5 DD 140420B5 DD 20969178 A DD20969178 A DD 20969178A DD 20969178 A DD20969178 A DD 20969178A DD 140420 B5 DD140420 B5 DD 140420B5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- chloroethyl
- cytostatic
- oxo
- salt
- oxazaphosphorinane
- Prior art date
Links
- 239000000824 cytostatic agent Substances 0.000 title claims description 31
- 230000001085 cytostatic effect Effects 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 7
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 16
- 229960001101 ifosfamide Drugs 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 12
- 229940100198 alkylating agent Drugs 0.000 claims description 12
- 239000002168 alkylating agent Substances 0.000 claims description 12
- 159000000000 sodium salts Chemical class 0.000 claims description 9
- 229960004397 cyclophosphamide Drugs 0.000 claims description 8
- UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 claims description 8
- 229960000875 trofosfamide Drugs 0.000 claims description 6
- ZSZKJARKHWCBJK-UHFFFAOYSA-N 2-[[3-(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-yl]amino]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNP1(=O)OCCCN1CCCl ZSZKJARKHWCBJK-UHFFFAOYSA-N 0.000 claims description 5
- 229950008275 sufosfamide Drugs 0.000 claims description 4
- -1 alkali metal salt Chemical class 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 17
- 210000003932 urinary bladder Anatomy 0.000 description 13
- 206010028980 Neoplasm Diseases 0.000 description 9
- 201000011510 cancer Diseases 0.000 description 7
- ZNEWHQLOPFWXOF-UHFFFAOYSA-N coenzyme M Chemical compound OS(=O)(=O)CCS ZNEWHQLOPFWXOF-UHFFFAOYSA-N 0.000 description 7
- 229940006193 2-mercaptoethanesulfonic acid Drugs 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000002207 metabolite Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- 210000001635 urinary tract Anatomy 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 201000003146 cystitis Diseases 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 2
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 229960004308 acetylcysteine Drugs 0.000 description 2
- 239000004086 alkylating cytostatic agent Substances 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 238000001784 detoxification Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- OKVLRTXOHOBONS-UHFFFAOYSA-N 2-methyl-3-sulfanylpropane-1-sulfonic acid Chemical compound SCC(C)CS(O)(=O)=O OKVLRTXOHOBONS-UHFFFAOYSA-N 0.000 description 1
- ZZVDXRCAGGQFAK-UHFFFAOYSA-N 2h-oxazaphosphinine Chemical class N1OC=CC=P1 ZZVDXRCAGGQFAK-UHFFFAOYSA-N 0.000 description 1
- OBDVFOBWBHMJDG-UHFFFAOYSA-N 3-mercapto-1-propanesulfonic acid Chemical compound OS(=O)(=O)CCCS OBDVFOBWBHMJDG-UHFFFAOYSA-N 0.000 description 1
- HMEJBVOVTCTWRG-UHFFFAOYSA-N 6-sulfanylhexane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCCCS HMEJBVOVTCTWRG-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-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
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- XOGTZOOQQBDUSI-UHFFFAOYSA-M Mesna Chemical compound [Na+].[O-]S(=O)(=O)CCS XOGTZOOQQBDUSI-UHFFFAOYSA-M 0.000 description 1
- MRIMWDXKBILRPB-UHFFFAOYSA-N O=P1NCCCO1 Chemical class O=P1NCCCO1 MRIMWDXKBILRPB-UHFFFAOYSA-N 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 229960002092 busulfan Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960004630 chlorambucil Drugs 0.000 description 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005584 early death Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002008 hemorrhagic effect Effects 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960001924 melphalan Drugs 0.000 description 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- RGFHLQGHCYAKTD-UHFFFAOYSA-N oxazaphosphinane Chemical compound C1CONPC1 RGFHLQGHCYAKTD-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000002633 shock therapy Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- LHUAYJZGTZYKSW-UHFFFAOYSA-M sodium;1-sulfanylpropane-1-sulfonate Chemical compound [Na+].CCC(S)S([O-])(=O)=O LHUAYJZGTZYKSW-UHFFFAOYSA-M 0.000 description 1
- PXRGAUOLIWDZSW-UHFFFAOYSA-M sodium;6-sulfanylhexane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCCCCS PXRGAUOLIWDZSW-UHFFFAOYSA-M 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960004560 triaziquone Drugs 0.000 description 1
- PXSOHRWMIRDKMP-UHFFFAOYSA-N triaziquone Chemical compound O=C1C(N2CC2)=C(N2CC2)C(=O)C=C1N1CC1 PXSOHRWMIRDKMP-UHFFFAOYSA-N 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2756018A DE2756018C2 (de) | 1977-12-14 | 1977-12-14 | Verwendung von Salzen von Mercaptoalkansulfonsäuren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DD140420A5 DD140420A5 (de) | 1980-03-05 |
| DD140420B5 true DD140420B5 (de) | 1995-06-14 |
Family
ID=6026256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD20969178A DD140420B5 (de) | 1977-12-14 | 1978-12-12 | Verfahren zur Herstellung detoxifizierter Zubereitungen von Cytostatika |
Country Status (15)
| Country | Link |
|---|---|
| AR (1) | AR216563A1 (el) |
| AT (1) | AT358162B (el) |
| CA (1) | CA1117015A (el) |
| DD (1) | DD140420B5 (el) |
| DE (1) | DE2756018C2 (el) |
| EG (1) | EG14057A (el) |
| GR (1) | GR68356B (el) |
| HU (1) | HU179915B (el) |
| IE (1) | IE47609B1 (el) |
| IL (1) | IL56097A (el) |
| MC (1) | MC1229A1 (el) |
| PL (1) | PL211758A1 (el) |
| PT (1) | PT68904A (el) |
| YU (1) | YU291978A (el) |
| ZA (1) | ZA786662B (el) |
-
1977
- 1977-12-14 DE DE2756018A patent/DE2756018C2/de not_active Expired
-
1978
- 1978-11-27 ZA ZA00786662A patent/ZA786662B/xx unknown
- 1978-11-29 GR GR57769A patent/GR68356B/el unknown
- 1978-11-30 IL IL56097A patent/IL56097A/xx unknown
- 1978-12-05 IE IE2404/78A patent/IE47609B1/en unknown
- 1978-12-06 AR AR274705A patent/AR216563A1/es active
- 1978-12-06 AT AT871078A patent/AT358162B/de not_active IP Right Cessation
- 1978-12-12 CA CA000317744A patent/CA1117015A/en not_active Expired
- 1978-12-12 PT PT68904A patent/PT68904A/pt unknown
- 1978-12-12 MC MC781346A patent/MC1229A1/fr unknown
- 1978-12-12 DD DD20969178A patent/DD140420B5/de active IP Right Maintenance
- 1978-12-13 EG EG702/78A patent/EG14057A/xx active
- 1978-12-13 HU HU78AA913A patent/HU179915B/hu unknown
- 1978-12-14 PL PL21175878A patent/PL211758A1/xx unknown
- 1978-12-16 YU YU02919/78A patent/YU291978A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR216563A1 (es) | 1979-12-28 |
| DD140420A5 (de) | 1980-03-05 |
| DE2756018B1 (de) | 1979-03-29 |
| IL56097A0 (en) | 1979-01-31 |
| DE2756018C2 (de) | 1979-11-22 |
| IE782404L (en) | 1979-06-14 |
| PL211758A1 (el) | 1980-02-11 |
| IE47609B1 (en) | 1984-05-02 |
| PT68904A (en) | 1979-01-01 |
| YU291978A (en) | 1984-02-29 |
| ATA871078A (de) | 1980-01-15 |
| GR68356B (el) | 1981-12-23 |
| CA1117015A (en) | 1982-01-26 |
| ZA786662B (en) | 1979-10-31 |
| IL56097A (en) | 1981-09-13 |
| EG14057A (en) | 1982-09-30 |
| HU179915B (en) | 1983-01-28 |
| MC1229A1 (fr) | 1979-10-26 |
| AT358162B (de) | 1980-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EP | Request for examination under paragraph 12(1) filed | ||
| B5 | Patent specification, 2nd publ. accord. to extension act | ||
| BAUF | Maintained restricted (sect. 12/3 extension act) |