DE2323744C3 - 4,4'-Bismethylen-(3-methoxy-2-naphthoesäure-triamcinolon-acetonidester) und Verfahren zu dessen Herstellung - Google Patents
4,4'-Bismethylen-(3-methoxy-2-naphthoesäure-triamcinolon-acetonidester) und Verfahren zu dessen HerstellungInfo
- Publication number
- DE2323744C3 DE2323744C3 DE2323744A DE2323744A DE2323744C3 DE 2323744 C3 DE2323744 C3 DE 2323744C3 DE 2323744 A DE2323744 A DE 2323744A DE 2323744 A DE2323744 A DE 2323744A DE 2323744 C3 DE2323744 C3 DE 2323744C3
- Authority
- DE
- Germany
- Prior art keywords
- triamcinolone acetonide
- methoxy
- naphthoic acid
- preparation
- bismethylene
- Prior art date
- 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
Links
- 229960002117 triamcinolone acetonide Drugs 0.000 title claims description 13
- -1 3-methoxy-2-naphthoic acid triamcinolone acetonide ester Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 4
- 239000002253 acid Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical group C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VGNGFRZTSUWCLT-UHFFFAOYSA-N 4-[(3-carboxy-2-methoxynaphthalen-1-yl)methyl]-3-methoxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC(=C3OC)C(O)=O)=C(OC)C(C(O)=O)=CC2=C1 VGNGFRZTSUWCLT-UHFFFAOYSA-N 0.000 description 4
- 201000004624 Dermatitis Diseases 0.000 description 4
- 208000010668 atopic eczema Diseases 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 238000004820 blood count Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003470 adrenal cortex hormone Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- 229960001334 corticosteroids Drugs 0.000 description 2
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 125000001153 fluoro group Chemical class F* 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 208000017520 skin disease Diseases 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- LFAUJRVUXMMOGY-UHFFFAOYSA-N 4-[(3-carbonochloridoyl-2-methoxynaphthalen-1-yl)methyl]-3-methoxynaphthalene-2-carbonyl chloride Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC(=C3OC)C(Cl)=O)=C(OC)C(C(Cl)=O)=CC2=C1 LFAUJRVUXMMOGY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 201000009053 Neurodermatitis Diseases 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 230000037374 absorbed through the skin Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 208000005005 intertrigo Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2323744A DE2323744C3 (de) | 1972-05-13 | 1973-05-10 | 4,4'-Bismethylen-(3-methoxy-2-naphthoesäure-triamcinolon-acetonidester) und Verfahren zu dessen Herstellung |
| CH675273A CH562773A5 (en:Method) | 1972-05-13 | 1973-05-11 | |
| GB2259773A GB1373900A (en) | 1972-05-13 | 1973-05-11 | Corticoid ester and method of preparing it |
| FR7317257A FR2195432B1 (en:Method) | 1972-05-13 | 1973-05-11 | |
| BE140705A BE810788A (fr) | 1972-05-13 | 1974-02-08 | Derive de l'acetonide de triamcinolone |
| US05/452,322 US4107161A (en) | 1972-05-13 | 1974-03-18 | Bis(triamcinolone acetonide)-4,4'-methylenebis-(3-methoxy-2-naphthoate) |
| US511075A US3899581A (en) | 1972-05-13 | 1974-10-01 | Triamcinolone acetonide derivative |
| US05/822,695 USRE29799E (en) | 1972-05-13 | 1977-08-08 | Triamcinolone acetonide derivative |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES403067A ES403067A1 (es) | 1972-05-13 | 1972-05-13 | Procedimiento para la obtencion de un ester del acido 4,4'-metilenbis-(3-metoxi-2-naftoico). |
| DE2323744A DE2323744C3 (de) | 1972-05-13 | 1973-05-10 | 4,4'-Bismethylen-(3-methoxy-2-naphthoesäure-triamcinolon-acetonidester) und Verfahren zu dessen Herstellung |
| US511075A US3899581A (en) | 1972-05-13 | 1974-10-01 | Triamcinolone acetonide derivative |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2323744A1 DE2323744A1 (de) | 1974-11-28 |
| DE2323744B2 DE2323744B2 (de) | 1978-03-02 |
| DE2323744C3 true DE2323744C3 (de) | 1978-11-23 |
Family
ID=27185265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2323744A Expired DE2323744C3 (de) | 1972-05-13 | 1973-05-10 | 4,4'-Bismethylen-(3-methoxy-2-naphthoesäure-triamcinolon-acetonidester) und Verfahren zu dessen Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3899581A (en:Method) |
| BE (1) | BE810788A (en:Method) |
| CH (1) | CH562773A5 (en:Method) |
| DE (1) | DE2323744C3 (en:Method) |
| FR (1) | FR2195432B1 (en:Method) |
| GB (1) | GB1373900A (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4084745A (en) * | 1976-07-27 | 1978-04-18 | Jones Robert J | Waste heat utilization system |
| NL8902513A (nl) * | 1989-10-10 | 1991-05-01 | Henri Bernard Peteri En Niels | Inrichting voor het leveren van hoeveelheden water met variabele temperaturen. |
| US5707981A (en) * | 1994-07-28 | 1998-01-13 | Psorial, L.L.C. | Synergistic pharmaceutical compositions |
| US5869104A (en) * | 1997-09-19 | 1999-02-09 | Taylor; Lesli A. | Method for treating dermatological conditions including impetigo |
| JP2008044935A (ja) * | 2006-07-20 | 2008-02-28 | Sicor Inc | 固体状無菌活性医薬成分を製造する方法 |
-
1973
- 1973-05-10 DE DE2323744A patent/DE2323744C3/de not_active Expired
- 1973-05-11 FR FR7317257A patent/FR2195432B1/fr not_active Expired
- 1973-05-11 CH CH675273A patent/CH562773A5/xx not_active IP Right Cessation
- 1973-05-11 GB GB2259773A patent/GB1373900A/en not_active Expired
-
1974
- 1974-02-08 BE BE140705A patent/BE810788A/xx not_active IP Right Cessation
- 1974-10-01 US US511075A patent/US3899581A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CH562773A5 (en:Method) | 1975-06-13 |
| DE2323744B2 (de) | 1978-03-02 |
| FR2195432A1 (en:Method) | 1974-03-08 |
| DE2323744A1 (de) | 1974-11-28 |
| GB1373900A (en) | 1974-11-13 |
| US3899581A (en) | 1975-08-12 |
| FR2195432B1 (en:Method) | 1978-07-28 |
| BE810788A (fr) | 1974-05-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BI | Miscellaneous see part 2 | ||
| C3 | Grant after two publication steps (3rd publication) |