Patent US3176098A successfully refreshed from Google Patents.
Patent US4009159A successfully refreshed from Google Patents.
US4009159A
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US
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Halogenated penam derivatives and the preparation thereof
Assignee: Astellas Pharma Inc
•
Filing: 1973-12-21
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Granted: 1977-02-22
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Expires: 1993-12-21
Abstract
Abstract A penam derivative having the formula: ##STR1## wherein X represents a halogen atom, and wherein R 1 represents an amino or acylamino, and R 3 represents a radical selected from the group consisting of carboxy, ester, acid amide, acid anhydride, acid halide, and acid azide.
Inventors
- 👤 Takashi Kamiya
- 👤 Yoshihisa Saito
- 👤 Tsutomu Teraji
- 👤 Osamu Nakaguti
- 👤 Teruo Oku
- 👤 Hitoshi Nakamura
- 👤 Masashi Hashimoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 16:02
CPC Classifications
C; C07; C07D; C07D499/00; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/09; C07D205/095
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
259 words
Penam derivatives having the formula ##STR23## wherein X represents a halogen atom, and wherein R 1 represents acylamino wherein said acyl substiuent is selected from the group consisting of formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl, acryloyl, crotonoyl, 2-methylacryloyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cycloheptylcarbonyl, cyclohexylacetyl, cycloheptylacetyl, cyclohexylpropionyl, cycloheptylpropionyl, dihydrobenzoyl, 2,4,6-cycloheptatrienylacetyl, dihydrophenylacetyl, methoxyacetyl, methylthioacetyl, 2-propenylthioacetyl, cyclohexylthioacetyl, cyclohexyloxyacetyl, dihydrophenoxyacetyl, dihydrophenylthioacetyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, dihydrophenoxycarbonyl, cycloheptyloxycarbonyl, benzoyl, toluoyl, naphthoyl, α- methylnaphthoyl, phthaloyl, tetrahydronaphthoyl, phenylacetyl, phenylpropionyl, phenylbutyryl, tolylacetyl, xylylacetyl, naphthylacetyl, tetrahydronaphthylacetyl, phenoxyacetyl, benzyloxycarbonyl, xylyloxycarbonyl, naphthoxycarbonyl, phenoxycarbonyl, 2-phenoxypropionyl, 2-phenoxybutyryl, 1H-tetrazolylacetyl, 2H-tetrazolylacetyl, thienylacetyl, thienylpropionyl, furylacetyl, piperazinylacetyl, pyrrolidinylacetyl, pyrrolidinylpropionyl, benzothiazolylacetyl, oxazolyacetyl, benzoxazolylacettyl, pyridylmethoxycarbonyl, 2-furyloxycarbonyl, 8-quinolyloxycarbonyl, trichloroethoxycarbonyl, tribromoethoxycarbonyl, 1 cyclo propylethoxycarbonyl, chloroacetyl, 2-chloropropionyl, trifluoroacetyl, phenylglycyl, p-aminophenylacetyl, p- nitrobenzyloxycarbonyl, o-bromo-benzyloxycarbonyl, o-nitrobenzyloxycarbonyl, p-methoxybenzyloxycarbonyl, 3,4-dimethoxybenzyloxycarbonyl, p- hydroxyphenylacetyl,2,5-dimethoxybenzoyl, 3-phenyl-5-methyl-4-oxazolylcarbonyl, 3-(2-chlorophenyl)-5-methyl-4-oxazolylcarbonyl, 3-(2,6-dichlorophenyl)- 5-methyl-4-oxazolylcarbonyl, 3-(2-chloro-6-fluorophenyl)-5-methyl-4- oxazolylcarbonyl, 2-cyanoacetyl, 2-(p-hydroxyphenyl)-2-(1-cyclopropylethoxy- carbonylamino)acetyl, 2-(sydonone-3-yl)acetyl and 3-(2-chlorophenyl)-5-methylisoxazole4-carbonyl; wherein the amino of said acyl substituent containing an amino is protected with a protective group selected from the group consisting of trichlorethoxycarbonyl, tribomoethoxycarbonyl, benzyloxycarbonyl, p- toluenesulfonyl, p-nitrobenzyloxycarbonyl, o-bromobenzyloxycarbonyl, o- nitrophenylsulfenyl, chloroacetyl, tribomoacetyl, formyl, tert-butoxycarbonyl, p-methoxybenzyloxycarbonyl, 3,4-dimethoxybenzyloxycarbonyl, 4-phenylazobenzyloxycarbonyl, 4-(4-methoxyphenylazo)benzyloxycarbonyl, pyridine- 1-oxide-2-methoxycarbonyl, 2-pyridylmethoxycarbonyl, 2-furyloxycarbonyl, diphenylmethoxycarbonyl, 1,1-dimethylpropoxycarbonyl, isopropoxycarbonyl, 1-cyclopropylethoxycarbonyl, phthaloyl, succinyl, 1-adamantyloxycarbonyl, 8-quinolyloxycarbonyl, trityl, 2-nitrophenylthio, 2,4-dinitrophenylthio, 2-hydroxybenzylidene, 2-hydroxy-5-chlorobenzylidene, 2-hydroxy- 1-naphthylmethylene, 3-hydroxy-4-pyridylmethylene, 1-methoxycarbonyl-2-propylidene, 1-ethoxycarbonyl-2-propylidene, 3-ethoxycarbonyl-2-butylidene, 1-acetyl-2-propylidene, 1-benzoyl-2-propylidene, 1-[N-(2-methoxyphenyl)carbamoyl]- 2-propylidene, 1-[N-(4-methoxyphenyl)carbamoyl]-2-propylidene, 2-ethoxycarbonylcyclohexylidene, 2-ethoxycarbonylcyclopentylidene, 2-acetylcyclohexylidene, 3,3-dimethyl-5-oxocyclohexylidene, monosilyl and disilyl; wherein the hydroxy of said acyl substituent containing a hydroxy is protected with a protective group selected from the group consisting of benzyloxycarbonyl, 4-nitrobenzyloxycarbonyl, 4-methoxybenzyloxycarbonyl, 3,4-dimethoxybenzyloxycarbonyl, 4-phenylazobenzyloxycarbonyl, 4-(4-methoxyphenylazo)benzyloxycarbonyl, tert-butoxycarbonyl, 1,1-dimethylpropoxycarbonyl, isopropoxycarbonyl, diphenylmethoxycarbonyl, 2-pyridylmethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, 2,2,2-tribromoethoxycarbonyl, 3-iodopropoxycarbonyl, 2-furfuryloxycarbonyl, 1-adamantyloxycarbonyl, 1-cyclopropylethoxycarbonyl, 8-quinolyloxycarbonyl, trifluouroacetyl, trifluoroacetyl, trityl, methoxymethyl, 2-nitrophenylthio, and 2,4-dinitrophenylthio, and R 3 represents a radical selected from the group consisting of
Claim 2
Dependent Claim
259 words
Penam derivatives having the formula ##STR23## wherein X represents a halogen atom, and wherein R 1 represents acylamino wherein said acyl substiuent is selected from the group consisting of formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl, acryloyl, crotonoyl, 2-methylacryloyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cycloheptylcarbonyl, cyclohexylacetyl, cycloheptylacetyl, cyclohexylpropionyl, cycloheptylpropionyl, dihydrobenzoyl, 2,4,6-cycloheptatrienylacetyl, dihydrophenylacetyl, methoxyacetyl, methylthioacetyl, 2-propenylthioacetyl, cyclohexylthioacetyl, cyclohexyloxyacetyl, dihydrophenoxyacetyl, dihydrophenylthioacetyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, dihydrophenoxycarbonyl, cycloheptyloxycarbonyl, benzoyl, toluoyl, naphthoyl, α- methylnaphthoyl, phthaloyl, tetrahydronaphthoyl, phenylacetyl, phenylpropionyl, phenylbutyryl, tolylacetyl, xylylacetyl, naphthylacetyl, tetrahydronaphthylacetyl, phenoxyacetyl, benzyloxycarbonyl, xylyloxycarbonyl, naphthoxycarbonyl, phenoxycarbonyl, 2-phenoxypropionyl, 2-phenoxybutyryl, 1H-tetrazolylacetyl, 2H-tetrazolylacetyl, thienylacetyl, thienylpropionyl, furylacetyl, piperazinylacetyl, pyrrolidinylacetyl, pyrrolidinylpropionyl, benzothiazolylacetyl, oxazolyacetyl, benzoxazolylacettyl, pyridylmethoxycarbonyl, 2-furyloxycarbonyl, 8-quinolyloxycarbonyl, trichloroethoxycarbonyl, tribromoethoxycarbonyl, 1 cyclo propylethoxycarbonyl, chloroacetyl, 2-chloropropionyl, trifluoroacetyl, phenylglycyl, p-aminophenylacetyl, p- nitrobenzyloxycarbonyl, o-bromo-benzyloxycarbonyl, o-nitrobenzyloxycarbonyl, p-methoxybenzyloxycarbonyl, 3,4-dimethoxybenzyloxycarbonyl, p- hydroxyphenylacetyl,2,5-dimethoxybenzoyl, 3-phenyl-5-methyl-4-oxazolylcarbonyl, 3-(2-chlorophenyl)-5-methyl-4-oxazolylcarbonyl, 3-(2,6-dichlorophenyl)- 5-methyl-4-oxazolylcarbonyl, 3-(2-chloro-6-fluorophenyl)-5-methyl-4- oxazolylcarbonyl, 2-cyanoacetyl, 2-(p-hydroxyphenyl)-2-(1-cyclopropylethoxy- carbonylamino)acetyl, 2-(sydonone-3-yl)acetyl and 3-(2-chlorophenyl)-5-methylisoxazole4-carbonyl; wherein the amino of said acyl substituent containing an amino is protected with a protective group selected from the group consisting of trichlorethoxycarbonyl, tribomoethoxycarbonyl, benzyloxycarbonyl, p- toluenesulfonyl, p-nitrobenzyloxycarbonyl, o-bromobenzyloxycarbonyl, o- nitrophenylsulfenyl, chloroacetyl, tribomoacetyl, formyl, tert-butoxycarbonyl, p-methoxybenzyloxycarbonyl, 3,4-dimethoxybenzyloxycarbonyl, 4-phenylazobenzyloxycarbonyl, 4-(4-methoxyphenylazo)benzyloxycarbonyl, pyridine- 1-oxide-2-methoxycarbonyl, 2-pyridylmethoxycarbonyl, 2-furyloxycarbonyl, diphenylmethoxycarbonyl, 1,1-dimethylpropoxycarbonyl, isopropoxycarbonyl, 1-cyclopropylethoxycarbonyl, phthaloyl, succinyl, 1-adamantyloxycarbonyl, 8-quinolyloxycarbonyl, trityl, 2-nitrophenylthio, 2,4-dinitrophenylthio, 2-hydroxybenzylidene, 2-hydroxy-5-chlorobenzylidene, 2-hydroxy- 1-naphthylmethylene, 3-hydroxy-4-pyridylmethylene, 1-methoxycarbonyl-2-propylidene, 1-ethoxycarbonyl-2-propylidene, 3-ethoxycarbonyl-2-butylidene, 1-acetyl-2-propylidene, 1-benzoyl-2-propylidene, 1-[N-(2-methoxyphenyl)carbamoyl]- 2-propylidene, 1-[N-(4-methoxyphenyl)carbamoyl]-2-propylidene, 2-ethoxycarbonylcyclohexylidene, 2-ethoxycarbonylcyclopentylidene, 2-acetylcyclohexylidene, 3,3-dimethyl-5-oxocyclohexylidene, monosilyl and disilyl; wherein the hydroxy of said acyl substituent containing a hydroxy is protected with a protective group selected from the group consisting of benzyloxycarbonyl, 4-nitrobenzyloxycarbonyl, 4-methoxybenzyloxycarbonyl, 3,4-dimethoxybenzyloxycarbonyl, 4-phenylazobenzyloxycarbonyl, 4-(4-methoxyphenylazo)benzyloxycarbonyl, tert-butoxycarbonyl, 1,1-dimethylpropoxycarbonyl, isopropoxycarbonyl, diphenylmethoxycarbonyl, 2-pyridylmethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, 2,2,2-tribromoethoxycarbonyl, 3-iodopropoxycarbonyl, 2-furfuryloxycarbonyl, 1-adamantyloxycarbonyl, 1-cyclopropylethoxycarbonyl, 8-quinolyloxycarbonyl, trifluouroacetyl, trifluoroacetyl, trityl, methoxymethyl, 2-nitrophenylthio, and 2,4-dinitrophenylthio, and R 3 represents a radical selected from the group consisting of
Claim 3
Dependent Claim
249 words
carboxy; 2. carboxy esters selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, cyclohexyl, cycloheptyl, vinyl, 1-propenyl, 2-propenyl, 3-butenyl, phenyl, xylyl, tolyl, naphthyl, benzyl, phenethyl, methoxymethyl, ethoxymethyl, methylthioethyl, methylthiomethyl, dimethylaminoethyl, diethylaminoethyl, phenoxymethyl, phenylthiomethyl, methylslfenylmethyl, phenylsulfenylmethyl, benzoylmethyl, toluoylmethyl, chloromethyl, bromomethyl, trichloroethyl, cyanomethyl, p-nitrophenyl, 2,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, pentachlorophenyl, p-methanesulfonylphenyl, 4-phenylazophenyl, 2,4-dinitrophenyl, p-chlorobenzyl, o-nitrobenzyl, p-methoxybenzyl, p-nitrobenzyl, 3,4,5-trimethoxybenzyl, bis(p-methoxyphenyl)methyl, pentachlorobenzyl, trichlorobenzyl, 3,5-di(tert)butyl-4-hydroxybenzyl, p-nitrophenylthiomethyl, p-nitrobenzoylmethyl, p-chlorobenzoylmethyl, esters of a thioalcohol, esters of a substituted thioalcohol, N-hydroxysuccinimide, N-hydroxyphthalimide, tetrahydrofuran, 1-cyclopropylethanol, 1-phenyl-3-methyl-5-pyrazolone, 3-hydroxypyridine, 2-hydroxymethylpyridine-1-oxide, 1-hydroxy-2(1H)- pyridine, dimethylhydroxyamine, diethylhydroxyamine, glycolamide, 88-hydroxy-quinoline, 2-hydroxymethylquinoline-1-oxide, oxime, methoxyacetylene, ethoxyacetylene, tert-butylethynyldimethylamine, tert-butylethynyldiethylamine, ethylethynyldiethylamine and 2-ethyl-5-(3-sulfophenyl)isoxazolium hydroxide inner salt; 3. acid amides selected from the group consisting of N-methyl acid amide, N-ethyl acid amide, N,N-dimethyl acid amide, N,N-diethyl acid amide, N-methyl-N-ethyl acid amide, the acid amide with imidazole and the acid amide with 4-substituted imidazole; 4. acid anhydrides selected from the group consisting of a dialkyl phosphate, dibenzyl phosphate, phosphoric acid, sulfuric acid, alkyl carbonate and aliphatic carboxylic acids selected from the group consisting of pivalic acid, pentanoic acid, isopentanoic acid, 2-ethylbutanoic acid, chloroacetic acid, crotonic acid, valeric acid, propionic acid, 3-chloro-3-pentanoic acid, 3-bromo-2-butenoic acid, phenylacetic acid, phenoxyacetic acid, furanacetic acid, thiophenacetic acid and aromatic carboxylic acids; 5. acid halides selected from the group consisting of acid chloride and acid bromide; 6. acid azide; 7. carboxy salts of a metal selected from the group consisting of sodium, potassium and magnesium; and 8. carboxy salts of an amine selected from the group consisting of methylamine, diethylamine, triethylamine, aniline, pyridine, picoline and N,N-dibenzylethylenediamine.
Claim 4
Dependent Claim
249 words
carboxy; 2. carboxy esters selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, cyclohexyl, cycloheptyl, vinyl, 1-propenyl, 2-propenyl, 3-butenyl, phenyl, xylyl, tolyl, naphthyl, benzyl, phenethyl, methoxymethyl, ethoxymethyl, methylthioethyl, methylthiomethyl, dimethylaminoethyl, diethylaminoethyl, phenoxymethyl, phenylthiomethyl, methylslfenylmethyl, phenylsulfenylmethyl, benzoylmethyl, toluoylmethyl, chloromethyl, bromomethyl, trichloroethyl, cyanomethyl, p-nitrophenyl, 2,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, pentachlorophenyl, p-methanesulfonylphenyl, 4-phenylazophenyl, 2,4-dinitrophenyl, p-chlorobenzyl, o-nitrobenzyl, p-methoxybenzyl, p-nitrobenzyl, 3,4,5-trimethoxybenzyl, bis(p-methoxyphenyl)methyl, pentachlorobenzyl, trichlorobenzyl, 3,5-di(tert)butyl-4-hydroxybenzyl, p-nitrophenylthiomethyl, p-nitrobenzoylmethyl, p-chlorobenzoylmethyl, esters of a thioalcohol, esters of a substituted thioalcohol, N-hydroxysuccinimide, N-hydroxyphthalimide, tetrahydrofuran, 1-cyclopropylethanol, 1-phenyl-3-methyl-5-pyrazolone, 3-hydroxypyridine, 2-hydroxymethylpyridine-1-oxide, 1-hydroxy-2(1H)- pyridine, dimethylhydroxyamine, diethylhydroxyamine, glycolamide, 88-hydroxy-quinoline, 2-hydroxymethylquinoline-1-oxide, oxime, methoxyacetylene, ethoxyacetylene, tert-butylethynyldimethylamine, tert-butylethynyldiethylamine, ethylethynyldiethylamine and 2-ethyl-5-(3-sulfophenyl)isoxazolium hydroxide inner salt; 3. acid amides selected from the group consisting of N-methyl acid amide, N-ethyl acid amide, N,N-dimethyl acid amide, N,N-diethyl acid amide, N-methyl-N-ethyl acid amide, the acid amide with imidazole and the acid amide with 4-substituted imidazole; 4. acid anhydrides selected from the group consisting of a dialkyl phosphate, dibenzyl phosphate, phosphoric acid, sulfuric acid, alkyl carbonate and aliphatic carboxylic acids selected from the group consisting of pivalic acid, pentanoic acid, isopentanoic acid, 2-ethylbutanoic acid, chloroacetic acid, crotonic acid, valeric acid, propionic acid, 3-chloro-3-pentanoic acid, 3-bromo-2-butenoic acid, phenylacetic acid, phenoxyacetic acid, furanacetic acid, thiophenacetic acid and aromatic carboxylic acids; 5. acid halides selected from the group consisting of acid chloride and acid bromide; 6. acid azide; 7. carboxy salts of a metal selected from the group consisting of sodium, potassium and magnesium; and 8. carboxy salts of an amine selected from the group consisting of methylamine, diethylamine, triethylamine, aniline, pyridine, picoline and N,N-dibenzylethylenediamine.
Claim 5
Dependent Claim
58 words
The penam derivative of claim 1, wherein X is selected from the group consisting of bromo and chloro; R 1 is selected from the group consisting of 2-cyanoacetamido, 2-phenylacetamido, 2-phenoxyacetamido, N-(2,2,2-trichloroethoxycarbonyl)phenylglycylamino, 2-(p-hydroxyphenyl)- 2-(1-cyclopropylethoxycarbonylamino)acetamido,2-(thiophene-2-yl)- acetamido, 2-(sydonone-3-yl)acetamido, 2-(1H-tetrazole-1-yl)-acetamido and 3-(2-chlorophenyl)-5-methylisoxazole-4-carbonamido; and R 3 is selected from the group consisting of carboxy, methyl ester, 1-cyclopropylethyl ester, 2,2,2-trichloroethyl ester and 4-hydroxy-3,5-ditertiarybutylbenzyl ester.
Claim 6
Dependent Claim
10 words
The penam derivative of claim 2 which is 2,2,2-trichloroethyl 6-(2-cyanoacetamido)-2-methyl-2-bromomethylpenam-3-carboxylate.
Claim 7
Dependent Claim
10 words
The penam derivative of claim 2 which is 1-cyclopropylethyl 6-(2-phenylacetamido)-2-methyl-2-bromomethylpenam-3-carboxylate.
Claim 8
Dependent Claim
10 words
The penam derivative of claim 2 which is 2,2,2-trichloroethyl 6-(2-phenylacetamido)-2-methyl-2-bromomethylpenam-3-carboxylate.
Claim 9
Dependent Claim
10 words
The penam derivative of claim 2 which is 2,2,2-trichloroethyl 6-(2-phenylacetamido)-2-methyl-2-chloromethylpenam-3-carboxylate.
Claim 10
Dependent Claim
12 words
The penam derivative of claim 2 which is 4-hydroxy-3, 5-ditertiarybutylbenzyl 6-(2-phenylacetamido)-2-methyl-2-bromomethylpenam- 3-carboxylate.
Claim 11
Dependent Claim
11 words
The penam derivative of claim 2 which is 6-(2-phenoxyacetamido)- 2-methyl-2-bromomethylpenam-3-carboxylic acid.
Claim 12
Dependent Claim
10 words
The penam derivative of claim 2 which is methyl 6-(2-phenoxyacetamido-2-methyl-2-bromomethylpenam-3-carboxylate.
Claim 13
Dependent Claim
10 words
The penam derivative of claim 2 which is methyl 6-(2-phenoxyacetamido)-2-methyl-2-chloromethylpenam-3-carboxylate.
Claim 14
Dependent Claim
10 words
The penam derivative of claim 2 which is 2,2,2-trichloroethyl 6-(2-phenoxyacetamido)-2-methyl-2-bromomethylpenam-3-carboxylate.
Claim 15
Dependent Claim
11 words
The penam derivative of claim 2 which is 2,2,2-trichloroethyl 6-[N-(2,2,2-trichloroethoxycarbonyl)-phenylglycyl]amino-2-methyl-2 -bromomethylpenam-3-carboxylate.
Claim 16
Dependent Claim
11 words
The penam derivative of claim 2 which is 2,2,2-trichloroethyl 6-[N-(2,2,2-trichloroethoxycarbonyl)-phenylglycyl]amino-2-methyl-2-chloromethylpenam- 3-carboxylate.
Claim 17
Dependent Claim
11 words
The penam derivative of claim 2 which is 2,2,2-trichloroethyl 6-[2-(p-hydroxyphenyl)-2-(1-cyclopropyl-ethoxy)carbonylamino]-2- methyl-2-bromomethylpenam-3-carboxylate.
Claim 18
Dependent Claim
10 words
The penam derivative of claim 2 which is 2,2,2-trichloroethyl 6-[2-(thiophene-2-yl)acetamido]-2-methyl-2-bromomethylpenam-3-carboxylate.
Claim 19
Dependent Claim
10 words
The penam derivative of claim 2 which is 2,2,2-trichloroethyl 6-[2-(sydonone-3-yl)acetamido]-2-methyl-2-bromomethylpenam-3-carboxylate.
Claim 20
Dependent Claim
10 words
The penam derivative of claim 2 which is 2,2,2-trichloroethyl 6-[2-(1H-tetrazole-1-yl)acetamido]-2-methyl-2-bromomethylpenam-3-carboxylate.
Claim 21
Dependent Claim
10 words
The penam derivative of claim 2 which is 2,2,2-trichloroethyl 6-[3-(2-chlorophenyl)-5-methylisoxazole-4-carbonamido]-2-methyl-2-bromomethylpenam-3-carboxylate.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1980-02-22 | 1980-08-23 | 1981-02-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-22 | 1984-08-23 | 1985-02-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-22 | 1988-08-23 | 1989-02-22 | $7700.00 | Window Closed / Lapsed |